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Chemistry

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Also known as: 58-25-3, Methaminodiazepoxide, Librium, Chlordiazepoxid, Librelease, Libritabs

Molecular Formula

C₁₆H₁₄ClN₃O

Molecular Weight

299.75 g/mol

InChI Key

BUCORZSTKDOEKQ-UHFFFAOYSA-N

FDA UNII

6RZ6XEZ3CR

An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal.

Chlordiazepoxide is a Benzodiazepine.

1 2D Structure

Chlordiazepoxide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine

2.1.2 InChI

InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9,21H,10H2,1H3

2.1.3 InChI Key

BUCORZSTKDOEKQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN=C1CN(C(=C2C=C(C=CC2=N1)Cl)C3=CC=CC=C3)O

2.2 Other Identifiers

2.2.1 UNII

6RZ6XEZ3CR

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 7 Chloro 2 Methylamino 5 Phenyl 3h 1,4 Benzodiazepine 4 Oxide

2. 7 Chloro N Methyl 5 Phenyl 3h 1,4 Benzodiazepin 2 Amine 4 Oxide

3. 7-chloro-2-methylamino-5-phenyl-3h-1,4-benzodiazepine-4-oxide

4. 7-chloro-n-methyl-5-phenyl-3h-1,4-benzodiazepin-2-amine 4-oxide

5. Chlordiazepoxide Hydrobromide

6. Chlordiazepoxide Hydrochloride

7. Chlordiazepoxide Monohydrochloride

8. Chlordiazepoxide Perchlorate

9. Chlozepid

10. Elenium

11. Hydrobromide, Chlordiazepoxide

12. Hydrochloride, Chlordiazepoxide

13. Librium

14. Methaminodiazepoxide

15. Monohydrochloride, Chlordiazepoxide

16. Perchlorate, Chlordiazepoxide

2.3.2 Depositor-Supplied Synonyms

1. 58-25-3

2. Methaminodiazepoxide

3. Librium

4. Chlordiazepoxid

5. Librelease

6. Libritabs

7. Clopoxide

8. Radepur

9. Lygen

10. 7-chloro-n-methyl-5-phenyl-3h-1,4-benzodiazepin-2-amine 4-oxide

11. 3h-1,4-benzodiazepin-2-amine, 7-chloro-n-methyl-5-phenyl-, 4-oxide

12. 7-chloro-4-hydroxy-n-methyl-5-phenyl-3h-1,4-benzodiazepin-2-imine

13. Chlordiazepoxide Civ

14. Chlozepid

15. Elenium

16. Chlorodiazepoxide

17. Chloridiazepide

18. Helogaphen

19. Kalmocaps

20. Viopsicol

21. Control

22. Decacil

23. Ifibrium

24. Librinin

25. Menrium

26. Mesural

27. Mildmen

28. Napoton

29. Psicosan

30. Risolid

31. Silibrin

32. Tropium

33. 6rz6xez3cr

34. Zetran

35. Chembl451

36. 7-chloro-2-(methylamino)-5-phenyl-3h-1,4-benzodiazepine 4-oxide

37. Disarim

38. Sonimen

39. Zeisin

40. Clordiazepossido

41. Eden-psich

42. Chlordiazepoxidum

43. Chlordiazepoxydum

44. 3h-1,4-benzodiazepine, 7-chloro-2-(methylamino)-5-phenyl-, 4-oxide

45. Clordiazepoxido

46. Chloradiazepoxide

47. Balance (pharmaceutical)

48. Dsstox_cid_26022

49. Dsstox_rid_81295

50. Dsstox_gsid_46022

51. Clordiazepossido [italian]

52. Chlordiazepoxidum [inn-latin]

53. Clordiazepoxido [inn-spanish]

54. 7-chloro-2-methylamino-5-phenyl-3h-1,4-benzodiazepin-4-oxide

55. Cas-58-25-3

56. Libritabs (tn)

57. Smr000469226

58. Hsdb 3028

59. Einecs 200-371-0

60. Unii-6rz6xez3cr

61. 7-chloro-n-methyl-4-oxido-5-phenyl-3h-1,4-benzodiazepin-4-ium-2-amine

62. Chlordiazepoxide-hcl

63. 7-chlor-2-methylamino-5-phenyl-3h-1,4-benzodiazepin-4-oxid [german]

64. 7-cloro-2-metilamino-5-fenil-3h-1,4-benzodiazepina 4-ossido [italian]

65. Chlordiazepoxide [usp:inn:ban:jan]

66. Chlordiazep-oxide Hcl

67. 7-chlor-2-methylamino-5-phenyl-3h-1,4-benzodiazepin-4-oxid

68. 7-cloro-2-metilamino-5-fenil-3h-1,4-benzodiazepina 4-ossido

69. Spectrum2_001157

70. Spectrum4_000578

71. Spectrum5_001623

72. Schembl18474

73. Chlordiazepoxide [mi]

74. Kbiogr_001016

75. Mls001066622

76. Mls001424220

77. Mls003899195

78. Chlordiazepoxide [inn]

79. Chlordiazepoxide [jan]

80. Divk1c_000995

81. Schembl145243

82. Spbio_001113

83. Chlordiazepoxide [hsdb]

84. Chebi:3611

85. Gtpl3370

86. Chlordiazepoxide [vandf]

87. Chlordiazepoxide [mart.]

88. Chebi:94781

89. Hms503g11

90. Kbio1_000995

91. Chlordiazepoxide [who-dd]

92. Dtxsid40861935

93. Ninds_000995

94. Hms2052c19

95. Hms2231m10

96. Hms3373m10

97. Hms3394c19

98. 7-chloro-2-methylamino-5-phenyl-3h-1,4-benzodiazepine-4-oxide

99. Chlordiazepoxide (jp17/usp/inn)

100. Tox21_111567

101. Tox21_111568

102. 3h-1,4-benzodiazepin-2-amine,7-chloro-n-methyl-5-phenyl-,4-oxide

103. Bbl010791

104. Bdbm50007664

105. Stk597142

106. Zinc19632917

107. Chlordiazepoxide [orange Book]

108. Chlordiazepoxide Civ [usp-rs]

109. Akos005518509

110. Akos015963131

111. Ab06298

112. Ccg-101136

113. Chlordiazepoxide [ep Monograph]

114. Db00475

115. Nc00386

116. Chlordiazepoxide [usp Monograph]

117. Chlordiazepoxide 1.0 Mg/ml In Methanol

118. Idi1_000995

119. Menrium Component Chlordiazepoxide

120. Ncgc00246347-01

121. Ac-13012

122. Vs-02683

123. Limbitrol Component Chlordiazepoxide

124. Chlordiazepoxide Component Of Menrium

125. Db-053173

126. Chlordiazepoxide Component Of Limbitrol

127. Limbitrol Ds Component Chlordiazepoxide

128. D00267

129. Ab00053219-06

130. Chlordiazepoxide Component Of Limbitrol Ds

131. Q178566

132. W-105404

133. 7-chloro-2-(methylamino)-5-phenyl-3h-1,4-benzodiazepin-4-ium-4-olate

134. 7-chloro-2-(methylimino)-5-phenyl-2,3-dihydro-4h-1,4-benzodiazepin-4-ol

135. (1e,4e)-7-chloro-2-(methylamino)-5-phenyl-3h-benzo[e][1,4]diazepine 4-oxide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₄ClN₃O
Molecular Weight	299.75 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	299.0825398 g/mol
Monoisotopic Mass	299.0825398 g/mol
Topological Polar Surface Area	48.2 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	580
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Librium
PubMed Health	Chlordiazepoxide (By mouth)
Drug Classes	Antianxiety
Drug Label	Librium, the original chlordiazepoxide HCl and prototype for the benzodiazepine compounds, was synthesized and developed at Hoffmann-La Roche Inc. It is a versatile therapeutic agent of proven value for the relief of anxiety. Librium is among the...
Active Ingredient	Chlordiazepoxide hydrochloride
Dosage Form	Capsule
Route	Oral
Strength	25mg; 5mg; 10mg
Market Status	Prescription
Company	Valeant Pharm Intl

2 of 2
Drug Name	Librium
PubMed Health	Chlordiazepoxide (By mouth)
Drug Classes	Antianxiety
Drug Label	Librium, the original chlordiazepoxide HCl and prototype for the benzodiazepine compounds, was synthesized and developed at Hoffmann-La Roche Inc. It is a versatile therapeutic agent of proven value for the relief of anxiety. Librium is among the...
Active Ingredient	Chlordiazepoxide hydrochloride
Dosage Form	Capsule
Route	Oral
Strength	25mg; 5mg; 10mg
Market Status	Prescription
Company	Valeant Pharm Intl

4.2 Therapeutic Uses

Adjuvants, Anesthesia; Anti-Anxiety Agents, Benzodiazepine; GABA Modulators; Sedatives, Nonbarbiturate

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

MEDICATION (VET): 15-30% LEVEL IN FEED, PRODUCES ... /CNS DEPRESSION/ IN COWBIRDS; QUAILS (5-10% LEVEL) SHOW EXCITEMENT PHASE BEFORE ... /CNS DEPRESSION/. 3-10 MG/KG IP AGAINST AGGRESSIVE BEHAVIOR IN RATS. AS CNS DEPRESSANT (80 MG/KG) IN RATS & MICE. AS ADRENERGIC BLOCKING AGENT (20 MG/KG) IN MICE. IN ZOO ANIMALS, 4-25 MG/KG BY SUITABLE ROUTE OF ADMIN HAS TAMING EFFECT ON VICIOUS ANIMALS; BARBITURATES ARE USED AS ADJUNCTIVES. IN RHESUS MONKEYS AS ANTICONVULSANT (4.4 MG/KG IV) /FROM TABLE/

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 101

Chlordiazepoxide ... is used for ... the management of agitation associated with acute alcohol withdrawal.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1942

... AS PREMEDICATION IN ANESTHESIA & IN OBSTETRICS DURING LABOR. /BENZODIAZEPINES/

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 436

For more Therapeutic Uses (Complete) data for CHLORDIAZEPOXIDE (7 total), please visit the HSDB record page.

4.3 Drug Warning

CHLORDIAZEPOXIDE HYDROCHLORIDE REQUIRES ... PRECAUTIONS REGARDING ITS USE IN PT WITH KNOWN HYPERSENSITIVITY, ELDERLY & EXCESSIVELY DEPRESSED INDIVIDUALS, PREGNANT & LACTATING MOTHERS, PT WITH KNOWN RENAL & HEPATIC IMPAIRMENT, PT ON OTHER CNS DEPRESSANT DRUGS, & IN PT WITH EITHER A HISTORY OF DRUG ADDICTION OR INDISCRIMINANT ALTERATION OF DRUG DOSAGE. /CHLORDIAZEPOXIDE HYDROCHLORIDE/

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1006

Safety and efficacy of orally administered chlordiazepoxide ... in children younger than 6 years of age ... have not been established.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1942

The iv preparation reconstituted with 0.9% sodium chloride injection or sterile water for injection should not be given im /SRP: absorption from this site is very slow and variable/ injection.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1942

THE EFFECT OF NORMAL ORAL DOSES (10 MG 3 TIMES A DAY) OF CHLORDIAZEPOZIDE (LIBRIUM) WAS STUDIED IN A DOUBLE-BLIND CROSSOVER TRIAL IN 7 PATIENTS WITH RESPIRATORY FAILURE DUE PREDOMINANTLY TO CHRONIC BRONCHITIS. IN 6 PATIENTS THE DRUG CAUSED A HIGHLY SIGNIFICANT INCREASE IN MIXED VENOUS CARBON-DIOXIDE TENSION AND A SIGNIFICANT FALL IN FORCED EXPIRATORY VOLUME IN ONE SECOND. IT IS CONCLUDED THAT CHLORDIAZEPOXIDE IS CONTRAINDICATED IN PATIENTS WITH RESPIRATORY FAILURE DUE TO CHRONIC BRONCHITIS.

PMID:4137638 MODEL DG, BERRY DJ; LANCET 2 (OCT 12): 869-70 (1974)

For more Drug Warnings (Complete) data for CHLORDIAZEPOXIDE (13 total), please visit the HSDB record page.

4.4 Minimum/Potential Fatal Human Dose

A few deaths have been reported at doses greater than 700 mg of ... chlordiazepoxide.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 424

4.5 Drug Indication

For the management of anxiety disorders or for the short-term relief of symptoms of anxiety, withdrawal symptoms of acute alcoholism, and preoperative apprehension and anxiety.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Chlordiazepoxide has antianxiety, sedative, appetite-stimulating and weak analgesic actions. The drug seems to block EEG arousal from stimulation in the brain stem reticular formation. The drug has been studied extensively in many species of animals and these studies are suggestive of action on the limbic system of the brain, which recent evidence indicates is involved in emotional responses. Hostile monkeys were made tame by oral drug doses which did not cause sedation. Chlordiazepoxide revealed a "taming" action with the elimination of fear and aggression. The taming effect of chlordiazepoxide was further demonstrated in rats made vicious by lesions in the septal area of the brain. The drug dosage which effectively blocked the vicious reaction was well below the dose which caused sedation in these animals.

5.2 MeSH Pharmacological Classification

Anti-Anxiety Agents

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)

Adjuvants, Anesthesia

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)

GABA Modulators

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CHLORDIAZEPOXIDE

5.3.2 FDA UNII

6RZ6XEZ3CR

5.3.3 Pharmacological Classes

Benzodiazepines [CS]; Benzodiazepine [EPC]

5.4 ATC Code

N - Nervous system

N05 - Psycholeptics

N05B - Anxiolytics

N05BA - Benzodiazepine derivatives

N05BA02 - Chlordiazepoxide

5.5 Absorption, Distribution and Excretion

Route of Elimination

Chlordiazepoxide is excreted in the urine, with 1% to 2% unchanged and 3% to 6% as conjugate.

INCR DISAPPEARANCE RATES OF CHLORDIAZEPOXIDE & ITS METABOLITES WERE OBSERVED AFTER SINGLE PRETREATMENT DOSE TO MICE. INCR CLEARANCE WAS INSUFFICIENT TO EXPLAIN TOLERANCE OBSERVED AND THE POSSIBILITY OF ALTERED DRUG DISTRIBUTION BETWEEN BLOOD & BRAIN TISSUE CANNOT BE EXCLUDED.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 121

LEVELS OF (14)C WERE MAX IN TISSUES OF CYNOMOLGUS MONKEYS 2-6 HR AFTER ORAL DOSE OF CHLORDIAZEPOXIDE. BRAIN TO BLOOD CONCN RATIOS OF (14)C WERE GREATER THAN 1. CONCN OF (14)C WERE HIGHEST IN LIVER & KIDNEYS & LOWER IN HEART, LUNGS, SPLEEN, BRAIN, ADRENALS, PANCREAS & FAT. AFTER 24 HR, GI TRACT CONTAINED 15%, TISSUES 33%, URINE 34%, & FECES 1%.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 86

Chlordiazepoxide is absorbed more rapidly and predictably after oral than after intramuscular administration, but blood levels vary widely among individuals.

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 216

PLASMA CONCENTRATION-TIME CURVES OF CHLORDIAZEPOXIDE WERE SATISFACTORILY DESCRIBED BY A BI-EXPONENTIAL EXPRESSION CONSISTENT WITH A TWO-COMPARTMENT MODEL SYSTEM AFTER INTRAVENOUS DOSES TO HEALTHY MALE VOLUNTEERS. MEAN HALF-LIFE VALUES OF THE DISTRIBUTION AND ELIMINATION PHASE WERE 0.25 AND 9.4 HOURS, RESPECTIVELY, WHILE MEAN VALUES FOR VOLUMES OF THE CENTRAL COMPARTMENT (V1) AND THE OVERALL DISTRIBUTION (VDBETA) WERE 18 AND 31% OF BODY WEIGHT. DRUG ABSORPTION FROM IM DOSES WAS COMPARATIVELY SLOW AND ADEQUATE DESCRIPTION OF RESULTING PLASMA LEVELS OF CHLORDIAZEPOXIDE REQUIRED THE INCORPORATION OF A TWO-COMPARTMENT "MUSCLE MODEL" WHICH INCLUDED PRECIPITATED AND SOLUBILIZED DRUG IN MUSCLE TISSUE. DISTRIBUTION VOLUMES OF CHLORDIAZEPOXIDE WERE SIGNIFICANTLY LARGER IN FEMALE SUBJECTS THAN IN THE MALES, SUGGESTING MORE EXTENSIVE DRUG DISTRIBUTION AMONG FEMALES. CHLORDIAZEPOXIDE IS TAKEN UP BY THE RED CELLS TO ONLY A LIMITED EXTENT.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 17

For more Absorption, Distribution and Excretion (Complete) data for CHLORDIAZEPOXIDE (9 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Hepatic.

IN MAN & DOGS, BIOTRANSFORMATION RESULTS IN SUCCESSIVE HYDROLYSIS OF METHYLAMINO-SUBSTITUENT IN 2-POSITION & HYDROLYTIC FISSION OF RESULTANT LACTAM; 7-CHLORO-1,3-DIHYDRO-5-PHENYL-2H-1,4-BENZODIAZEPINE-2-ONE-4-OXIDE & N-(2-AMINO-5-CHLORO-ALPHA-PHENYL-BENZYLIDENE) GLYCINE-N-OXIDE ARE EXCRETED IN URINE.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 415

IN DOGS, 1% OF A DOSE OF LIBRIUM FOUND IN URINE AS OXAZEPAM GLUCURONIDE AND A FURTHER 1% IN FECES AS FREE OXAZEPAM GLUCURONIDE. THESE MINOR METABOLITES PRESUMABLY ARISE VIA LACTAM BY STEPS INVOLVING REDUCTION OF N-OXIDE FUNCTION.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 415

YIELDS 2-AMINO-7-CHLORO-5-PHENYL-3H-1,4-BENZODIAZEPINE-4-OXIDE IN MAN, IN MONKEY. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-14

YIELDS N-(2-AMINO-5-CHLORO-ALPHA-PHENYLBENZYLIDENE)-GLYCINE-N-OXIDE IN PSEUDOMONAS, IN CLOSTRIDIUM. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-14

... THE MAJOR ACTIVE METABOLITE /OF CHLORDIAZEPOXIDE IS/ DESMETHYLCHLORDIAZEPOXIDE ...

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 216

5.7 Biological Half-Life

24-48 hours

The elimination half-life of the major active metabolite, desmethylchlordiazepoxide, ranges from one to four days ...

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 216

PLASMA CONCENTRATION TIME CURVES OF CHLORDIAZEPOXIDE WERE SATISFACTORILY DESCRIBED BY A BI-EXPONENTIAL EXPRESSION CONSISTENT WITH A TWO COMPARTMENT MODEL SYSTEM AFTER INTRAVENOUS DOSES TO HEALTHY MALE VOLUNTEERS. MEAN HALF-LIFE VALUES OF THE DISTRIBUTION AND ELIMINATION PHASE WERE 0.25 AND 9.4 HOURS, RESPECTIVELY ...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 17

THE DISPOSITION OF CHLORDIAZEPOXIDE (CDP), 50 MG INFUSED IV OVER 10 MINUTES, WAS STUDIED IN NORMAL SUBJECTS AND IN PATIENTS WITH BIOPSY-PROVEN CIRRHOSIS. IN THE NORMAL SUBJECTS, MEAN KINETIC PARAMETER WAS HALF-LIFE (BETA), 10.0 HOURS. VALUE IN CIRRHOTIC PATIENTS WAS HALF-LIFE (BETA), 34.9 HOURS.

PMID:455893 SELLERS EM ET AL; CLIN PHARMACOL THER 26 (2): 240-6 (1979)

Half-life: 5-30 hr /From table/

Gossel, T.A., J.D. Bricker. Principles of Clinical Toxicology. 3rd ed. New York, NY: Raven Press, Ltd., 1994., p. 314

5.8 Mechanism of Action

Chlordiazepoxide binds to stereospecific benzodiazepine (BZD) binding sites on GABA (A) receptor complexes at several sites within the central nervous system, including the limbic system and reticular formation. This results in an increased binding of the inhibitory neurotransmitter GABA to the GABA(A) receptor. BZDs, therefore, enhance GABA-mediated chloride influx through GABA receptor channels, causing membrane hyperpolarization. The net neuro-inhibitory effects result in the observed sedative, hypnotic, anxiolytic, and muscle relaxant properties.

IN METHYLATED SPINAL CORD FROM 9-15-DAY-OLD-RATS, CHLORDIAZEPOXIDE ENHANCED EVOKED SYNAPTIC RESPONSES MEDIATED BY GAMMA-AMINOBUTYRIC ACID (GABA) AND POTENTIATED GABA-INDUCED DEPOLARIZATION OF PRIMARY AFFERENTS AND HYPERPOLARIZATION OF MOTOR NEURONS. THE GABA-POTENTIATING EFFECT OF CHLORDIAZEPOXIDE WAS INCREASED BY ELEVATED CL- IN THE MEDIUM, BUT DID NOT DEPEND ON THE CONCENTRATION OF K+. APPARENTLY, CHLORDIAZEPOXIDE MAY PROLONG THE LIFE SPAN OF THE CHLORINE IONOPHORE COUPLED WITH GABA RECEPTORS OF THE SPINAL CORD.

ABRAMETS II, KOMISSAROV IV; BYULL EKSP BIOL MED 94 (10): 58-61 (1982)

Currently, there is general agreement that most, if not all of the actions of benzodiazepines are a result of potentiation of the neural inhibition that is mediated by gamma-aminobutyric acid (GABA). This view is supported by behavioral and electrophysiological evidence that the effects of benzodiazepines are reduced or prevented by prior treatment with antagonists of gamma-aminobutyric acid (eg, bicuculline) or inhibitors of the synthesis of the transmitter (eg, thiosemicarbazide). ... Most attention has been focused on the ability of benzodiazepines to potentiate the actions of gamma-aminobutyric acid on neurons at all levels of the neuraxis. ... A substantial body of biochemical evidence has accumulated that suggests a close molecular association between sites of action for gamma-aminobutyric acid and the benzodiazepines. /Benzodiazepines/

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 345

A large body of electrophysiological and biochemical observations has linked the actions of benzodiazepines to the functions of receptor chloride ionophore systems that are regulated by gamma-aminobutyric acid. The evidence includes the ability of various benzodiazepines to potentiate the effects of exogenous gamma-aminobutyric acid or to enhance gamma-aminobutyric acid mediated presynaptic and postsynaptic inhibitory pathways. Further, specific sites for benzodiazepines have been characterized in cell membranes from brain, and their properties can be modified by gamma-aminobutyric acid and by chloride or related ions that are known to carry current through channels that are regulated by gamma-aminobutyric acid. ... Two different types of receptors for gamma-aminobutyric acid /are detected/ in hippocampal pyramidal cells; diazepam potentiates somatic responses to gamma-aminobutyric acid that involve increases in chloride conductance ... potentiation of responses to gamma-aminobutyric acid requires concentrations of benzodiazepines 10 to 100 fold greater than those achieved in the CSF during therapy ... These observations suggest that the anticonvulsant effects of the benzodiazepines may not depend entirely upon actions on gamma-aminobutyric acid-ergic neurotransmission or on channels for chloride ions. /Benzodiazepines/

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 465

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FABBRICA ITALIANA SINTETICI","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"DR. REDDY\\'S LABORATORIES","customerCountry":"INDIA","quantity":"20.00","actualQuantity":"20","unit":"KGS","unitRateFc":"726","totalValueFC":"14718.4","currency":"USD","unitRateINR":"53580","date":"12-Feb-2021","totalValueINR":"1071600","totalValueInUsd":"14718.4","indian_port":"Reddy r-SEZ\/Srikakulam","hs_no":"29339100","bill_no":"1000048","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"N\/A","customerAddress":"H.NO. 8-2-337,BESIDE TV9 OFFICE"},{"dataSource":"API Import","activeIngredients":"CHLORDIAZEPOXIDE","year":"2021","qtr":"Q1","strtotime":1613068200,"product":"CHLORDIAZEPOXIDE HYDROCHLORIDE USP\/EP","address":"NO.27,RACE COURSE ROAD,BANGALORE","city":"KARNATAKA","supplier":"F.I.S. FABBRICA ITALIANA SINTETICI","supplierCountry":"ITALY","foreign_port":"MILAN - MALPENSA","customer":"MICRO LABS LIMITED","customerCountry":"INDIA","quantity":"0.50","actualQuantity":"0.5","unit":"KGS","unitRateFc":"2400","totalValueFC":"1471.8","currency":"EUR","unitRateINR":"214320","date":"12-Feb-2021","totalValueINR":"107160","totalValueInUsd":"1471.8","indian_port":"MADRAS AIR","hs_no":"29339990","bill_no":"2733431","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"","customerAddress":"NO.27,RACE COURSE ROAD,BANGALORE"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q2","strtotime":1656009000,"product":"CHLORDIAZEPOXIDE HYDROCHLORIDE USP\/EP (IMPORT LIC. NO-P\/IMP-10137\/2022 DT- 10\/03\/2022)","address":"781, INDUSTRIAL AREA,,PHASE-II,","city":"CHANDIGARH,CHANDIGARH","supplier":"F.I.S. FABBRICA ITALIANA SINTETICI","supplierCountry":"ITALY","foreign_port":"NA","customer":"IND SWIFT LABORATORIES LIMITED","customerCountry":"INDIA","quantity":"40.00","actualQuantity":"40","unit":"KGS","unitRateFc":"380","totalValueFC":"16773.5","currency":"EUR","unitRateINR":"32714.8","date":"24-Jun-2022","totalValueINR":"1308592.32","totalValueInUsd":"16773.5","indian_port":"DELHI AIR","hs_no":"29339100","bill_no":"9259146","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"781, INDUSTRIAL AREA,,PHASE-II,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1706121000,"product":"CHLORDIAZEPOXIDE HYDROCHLORIDE (IMPORT LIC.NO-P\/IMP-10733\/2023 DT-08.12.2023)","address":"ALKEM HOUSE, DEVASHISH ADJACENT TO","city":"LOWER PAREL, MUMBAI. MAHARASHTRA","supplier":"F.I.S. FABBRICA ITALIANA SINTETICI","supplierCountry":"ITALY","foreign_port":"MILAN - MALPENSA","customer":"ALKEM LABORATORIES","customerCountry":"INDIA","quantity":"25.00","actualQuantity":"25","unit":"KGS","unitRateFc":"750","totalValueFC":"20822.9","currency":"EUR","unitRateINR":"69225","date":"25-Jan-2024","totalValueINR":"1730625","totalValueInUsd":"20822.9","indian_port":"Delhi Air","hs_no":"29339100","bill_no":"9832964","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"VIALE MILANO 26 36075 MONLECCHIO MAGGIANE (VI) , , ITALYSDNF ITALY","customerAddress":"ALKEM HOUSE, DEVASHISH ADJACENT TO"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1713378600,"product":"CHLORDIAZEPOXIDE HYDROCHLORIDE USP\/EP (IMPORT LIC.NO-P\/IMP-10115\/2024 DT-22.02.2024","address":"ALKEM HOUSE, DEVASHISH ADJACENT TO","city":"LOWER PAREL, MUMBAI. MAHARASHTRA","supplier":"F.I.S. FABBRICA ITALIANA SINTETICI","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"ALKEM LABORATORIES","customerCountry":"INDIA","quantity":"25.00","actualQuantity":"25","unit":"KGS","unitRateFc":"750","totalValueFC":"20668.1","currency":"EUR","unitRateINR":"69037.5","date":"18-Apr-2024","totalValueINR":"1725937.5","totalValueInUsd":"20668.1","indian_port":"Delhi Air","hs_no":"29339100","bill_no":"3080855","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"N\/A","customerAddress":"ALKEM HOUSE, DEVASHISH ADJACENT TO"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722796200,"product":"CHLORDIAZEPOXIDE HYDROCHLORIDE USP\/EP","address":"NO 31, RACE COURSE ROAD,BANGALORE","city":"BENGALURU,KARNATAKA","supplier":"F.I.S. FABBRICA ITALIANA SINTETICI","supplierCountry":"ITALY","foreign_port":"VENICE","customer":"MICRO LABS LIMITED","customerCountry":"INDIA","quantity":"11.00","actualQuantity":"11","unit":"KGS","unitRateFc":"1000","totalValueFC":"12097.8","currency":"EUR","unitRateINR":"92250","date":"05-Aug-2024","totalValueINR":"1014750","totalValueInUsd":"12097.8","indian_port":"Madras Air","hs_no":"29339100","bill_no":"4885814","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"VENICE","supplierAddress":"VIALE MILANO, 2636075 MONTECCHIO MAGGIORE(VI)SDNF ITALY","customerAddress":"NO 31, RACE COURSE ROAD,BANGALORE"}]

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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DOSAGE - CAPSULE;ORAL - 5MG;2.5MG

USFDA APPLICATION NUMBER - 12750

DOSAGE - CAPSULE;ORAL - 5MG

USFDA APPLICATION NUMBER - 85461

DOSAGE - CAPSULE;ORAL - 10MG

USFDA APPLICATION NUMBER - 85472

DOSAGE - CAPSULE;ORAL - 25MG

USFDA APPLICATION NUMBER - 85475

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ACTIVE PHARMA INGREDIENTS

15 API Suppliers

8 USDMF

4 CEP/COS

2 JDMF

5 EU WC

1 KDMF

7 NDC API

7 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

2 Drugs in Development

FINISHED DOSAGE FORMULATIONS

146 FDF Dossiers

119 FDA Orange Book

4 Europe

4 Canada

4 South Africa

15 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

CAPSULE;ORAL - 5MG;2.5MG

CAPSULE;ORAL - 5MG

CAPSULE;ORAL - 10MG

CAPSULE;ORAL - 25MG

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11 Sigachi Industries

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EXCIPIENTS BY APPLICATIONS

80 Fillers, Diluents & Binders

48 Coating Systems & Additives

34 Direct Compression

30 Controlled & Modified Release

23 Thickeners and Stabilizers

23 Granulation

21 Disintegrants & Superdisintegrants

16 Solubilizers

16 Lubricants & Glidants

16 Co-Processed Excipients

11 Topical