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2D Structure
Also known as: Famotidine, 76824-35-6, Gastridin, Famodil, Pepdine, Pepdul
Molecular Formula
C8H15N7O2S3
Molecular Weight
337.5  g/mol
InChI Key
XUFQPHANEAPEMJ-UHFFFAOYSA-N
FDA UNII
5QZO15J2Z8

A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion.
Famotidine is a Histamine-2 Receptor Antagonist. The mechanism of action of famotidine is as a Histamine H2 Receptor Antagonist.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-N'-sulfamoylpropanimidamide
2.1.2 InChI
InChI=1S/C8H15N7O2S3/c9-6(15-20(12,16)17)1-2-18-3-5-4-19-8(13-5)14-7(10)11/h4H,1-3H2,(H2,9,15)(H2,12,16,17)(H4,10,11,13,14)
2.1.3 InChI Key
XUFQPHANEAPEMJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=C(N=C(S1)N=C(N)N)CSCCC(=NS(=O)(=O)N)N
2.1.5 Isomeric SMILES
C1=C(N=C(S1)N=C(N)N)CSCC/C(=N/S(=O)(=O)N)/N
2.2 Other Identifiers
2.2.1 UNII
5QZO15J2Z8
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Famotidine

2. Famotidine Hydrochloride

3. Mk 208

4. Mk-208

5. Mk208

6. Ym 11170

7. Ym-11170

8. Ym11170

2.3.2 Depositor-Supplied Synonyms

1. Famotidine

2. 76824-35-6

3. Gastridin

4. Famodil

5. Pepdine

6. Pepdul

7. Pepcidine

8. Famoxal

9. Ganor

10. Pepcidac

11. Amfamox

12. Gastropen

13. Famosan

14. Fluxid

15. Gaster

16. Lecedil

17. Motiax

18. Muclox

19. Pepcid Ac

20. Quamatel

21. Ym-11170

22. Pepcid Rpd

23. Fadul

24. Mk-208

25. Famotidine (pepcid)

26. 3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-n-sulfamoylpropanimidamide

27. L 643341

28. Mk 208

29. Chebi:4975

30. Ym 11170

31. Nsc-757810

32. 3-(((2-((diaminomethylene)amino)thiazol-4-yl)methyl)thio)-n'-sulfamoylpropanimidamide

33. Xufqphaneapemj-uhfffaoysa-

34. 3-(((2-guanidinothiazol-4-yl)methyl)thio)-n-sulfamoylpropanimidamide

35. (1-amino-3-(((2-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)propylidene)sulfamide

36. Pepcid Ac Gelcaps

37. Smr000058961

38. Pepcid (tn)

39. Chembl902

40. 3-[[[2-[(aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]-n-(aminosulfonyl)propanimidamide

41. Sr-05000001440

42. 5qzo15j2z8

43. Ncgc00015446-05

44. Fo9

45. Propanimidamide, N'-(aminosulfonyl)-3-(((2-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)-

46. Prestwick_212

47. Cas-76824-35-6

48. Fluxid (tn)

49. Mfcd00079297

50. Hs-0054

51. Ym-1170

52. Famotidine [mi]

53. 3-(2-guanidinothiazol-4-ylmethylthio)-n1-sulfamoylpropionamide

54. Famotidine [inn]

55. Famotidine [jan]

56. Prestwick2_000104

57. Prestwick3_000104

58. Famotidine [hsdb]

59. Famotidine [usan]

60. Lopac-f-6889

61. F0530

62. Schembl972

63. Schembl974

64. Famotidine [vandf]

65. F 6889

66. Famotidine [mart.]

67. Famotidine [usp-rs]

68. Famotidine [who-dd]

69. N'-(aminosulfonyl)-3-([2-(diaminomethyleneamino)-4-thiazolyl]methylthio)propanamidine

70. Lopac0_000497

71. Bspbio_000088

72. Mls000028583

73. Mls000758205

74. Mls001423994

75. Bidd:gt0759

76. Bpbio1_000098

77. Famotidine (jp17/usp/inn)

78. Famotidine [orange Book]

79. Bdbm22891

80. Cid_5702160

81. Famotidine [ep Monograph]

82. Famotidine [usp Impurity]

83. Famotidine [usp Monograph]

84. Hms1568e10

85. Hms2051a07

86. Hms2089i12

87. Hms2095e10

88. Hms2231i22

89. Hms3261d15

90. Hms3712e10

91. Hms3884j03

92. Hy-b0377

93. Tox21_500497

94. Bdbm50103514

95. Pdsp1_000398

96. Pdsp2_000396

97. S2078

98. Stk527689

99. Akos005460541

100. Akos015994617

101. Ccg-100767

102. Ccg-220104

103. Ccg-221801

104. Nc00017

105. Sdccgsbi-0050481.p004

106. 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-n'-sulfamoylpro

107. Propanimidamide, 3-[[[2-[aminoiminomethyl)amino]-4-thiazoyl]methyl]thio]-n-(aminosulfonyl)

108. Ncgc00015446-01

109. Ncgc00015446-02

110. Ncgc00015446-03

111. Ncgc00015446-04

112. Ncgc00015446-06

113. Ncgc00015446-08

114. Ncgc00018276-01

115. Ncgc00018276-02

116. Ncgc00093899-01

117. Ncgc00093899-02

118. Ncgc00093899-03

119. Ncgc00188952-01

120. Ncgc00261182-01

121. (1z)-3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-n'-sulfamoylpropanimidamide

122. (1z)-n'-(aminosulfonyl)-3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)thio]propanimidamide

123. Ac-11713

124. Ac-31723

125. Pepcid Complete Component Famotidine

126. Sbi-0050481.p003

127. Eu-0100497

128. Famotidine Component Of Pepcid Complete

129. D00318

130. Ab00383032_11

131. 824f356

132. A838850

133. A899959

134. L003830

135. L013386

136. Sr-01000075883

137. Sr-01000075883-1

138. Sr-05000001440-1

139. Sr-05000001440-2

140. Famotidine, British Pharmacopoeia (bp) Reference Standard

141. Famotidine, European Pharmacopoeia (ep) Reference Standard

142. Famotidine, United States Pharmacopeia (usp) Reference Standard

143. 3-[(2-guanidinothiazol-4-yl)methylsulfanyl]-n-sulfamoyl-propanamidine

144. Famotidine, Pharmaceutical Secondary Standard; Certified Reference Material

145. 3-((((2-(diaminomethylene)amino)-4-thiazolyl)methyl)thio)-n-sulfamoylpropionamidine

146. 3-(2-(diaminomethyleneamino)-1,3-thiazol-4-yl)methylthio)-n'- Sulfamoylpropionamidine

147. 3-[2-(diaminomethyleneamino] Thiazol-4-ylmethylthio]-n-sulphamoyl Propionamidine

148. Famotidine For System Suitability, European Pharmacopoeia (ep) Reference Standard

149. 3-[({2-[(diaminomethylene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-n'-sulfamoylpropanimidamide

150. 3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-n''-sulfamoylpropanimidamide

2.4 Create Date
2006-03-07
3 Chemical and Physical Properties
Molecular Weight 337.5 g/mol
Molecular Formula C8H15N7O2S3
XLogP3-0.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass337.04493627 g/mol
Monoisotopic Mass337.04493627 g/mol
Topological Polar Surface Area238 Ų
Heavy Atom Count20
Formal Charge0
Complexity469
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 10  
Drug NameFamotidine
Active IngredientFamotidine
Dosage FormInjectable; Tablet; Tablet, chewable; For suspension; Suspension
Routeinjection; Injection; Oral
Strength40mg/5ml; 10mg; 10mg/ml; 40mg; 20mg
Market StatusTentative Approval; Over the Counter; Prescription
CompanyNavinta; Ranbaxy; Wockhardt; Bedford; Ivax Sub Teva Pharms; Marsam Pharms; Fresenius Kabi Usa; Hi-tech Pharma; Hikma Maple; Teva; Apotex; Perrigo; Alembic Pharms; Lupin; Dr Reddys Labs; Carlsbad; Agila Speclts; Mylan; Novel Labs

2 of 10  
Drug NameFamotidine preservative free
PubMed HealthFamotidine
Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
Drug LabelThe active ingredient in PEPCID (famotidine) is a histamine H2-receptor antagonist. Famotidine is N'-(aminosulfonyl)-3-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl]thio]propanimidamide. The empirical formula of famotidine is C8H15N7O2S3 and it..
Active IngredientFamotidine
Dosage FormInjectable
RouteInjection
Strength10mg/ml
Market StatusPrescription
CompanyBedford; Fresenius Kabi Usa; Hikma Maple; Bedford Labs; Agila Speclts

3 of 10  
Drug NameFamotidine preservative free in plastic container
PubMed HealthFamotidine (By mouth)
Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
Active IngredientFamotidine
Dosage FormInjectable
RouteInjection
Strength0.4mg/ml
Market StatusPrescription
CompanyBaxter Hlthcare

4 of 10  
Drug NamePepcid
PubMed HealthFamotidine
Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
Drug LabelThe active ingredient in Famotidine Injection, USP is a histamine H2-receptor antagonist. Famotidine is [1-Amino-3-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl]thio]propylidene] sulfamide. Its structural formula is:C8H15N7O2S3 MW 337.4...
Active IngredientFamotidine
Dosage FormTablet; For suspension
RouteOral
Strength40mg/5ml; 40mg; 20mg
Market StatusPrescription
CompanyMarathon Pharms; Salix Pharms

5 of 10  
Drug NamePepcid ac
Active IngredientFamotidine
Dosage FormTablet; Tablet, chewable
RouteOral
Strength10mg; 20mg
Market StatusOver the Counter
CompanyMcneil Cons

6 of 10  
Drug NameFamotidine
Active IngredientFamotidine
Dosage FormInjectable; Tablet; Tablet, chewable; For suspension; Suspension
Routeinjection; Injection; Oral
Strength40mg/5ml; 10mg; 10mg/ml; 40mg; 20mg
Market StatusTentative Approval; Over the Counter; Prescription
CompanyNavinta; Ranbaxy; Wockhardt; Bedford; Ivax Sub Teva Pharms; Marsam Pharms; Fresenius Kabi Usa; Hi-tech Pharma; Hikma Maple; Teva; Apotex; Perrigo; Alembic Pharms; Lupin; Dr Reddys Labs; Carlsbad; Agila Speclts; Mylan; Novel Labs

7 of 10  
Drug NameFamotidine preservative free
PubMed HealthFamotidine
Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
Drug LabelThe active ingredient in PEPCID (famotidine) is a histamine H2-receptor antagonist. Famotidine is N'-(aminosulfonyl)-3-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl]thio]propanimidamide. The empirical formula of famotidine is C8H15N7O2S3 and it..
Active IngredientFamotidine
Dosage FormInjectable
RouteInjection
Strength10mg/ml
Market StatusPrescription
CompanyBedford; Fresenius Kabi Usa; Hikma Maple; Bedford Labs; Agila Speclts

8 of 10  
Drug NameFamotidine preservative free in plastic container
PubMed HealthFamotidine (By mouth)
Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
Active IngredientFamotidine
Dosage FormInjectable
RouteInjection
Strength0.4mg/ml
Market StatusPrescription
CompanyBaxter Hlthcare

9 of 10  
Drug NamePepcid
PubMed HealthFamotidine
Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
Drug LabelThe active ingredient in Famotidine Injection, USP is a histamine H2-receptor antagonist. Famotidine is [1-Amino-3-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl]thio]propylidene] sulfamide. Its structural formula is:C8H15N7O2S3 MW 337.4...
Active IngredientFamotidine
Dosage FormTablet; For suspension
RouteOral
Strength40mg/5ml; 40mg; 20mg
Market StatusPrescription
CompanyMarathon Pharms; Salix Pharms

10 of 10  
Drug NamePepcid ac
Active IngredientFamotidine
Dosage FormTablet; Tablet, chewable
RouteOral
Strength10mg; 20mg
Market StatusOver the Counter
CompanyMcneil Cons

4.2 Therapeutic Uses

Anti-Ulcer Agents; Histamine H2 Antagonists

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


Famotidine is currently the drug of choice for initial treatment and maintenance therapy in most patients with uncomplicated gastric or duodenal ulcer. ... A single bedtime dose of famotidine 40 mg is as efficatious as previously recommended multidose regimens and increases compliance.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 892


Histamine H2-receptor antagonists are indicated in the short-term treatment of active duodenal ulcer. They are also indicated (at reduce dosage) in the prevention of duodenal ulcer recurrence in selected patients. /Histamine H2-receptor antagonists; Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 1611


Famotidine ... /is/ indicated in the short-term treatment of active benign gastric ulcer. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 1611


For more Therapeutic Uses (Complete) data for FAMOTIDINE (12 total), please visit the HSDB record page.


4.3 Drug Warning

Although appropriate studies on the relationship of age to the effects of these medicines /cimetidine, famotidine, and ranitidine/ have not been performed in the geriatric population, no geriatrics-specific problems have been documented to date. However, confusion is more likely to occur in elderly patients with impaired hepatic or renal function.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 1613


Adverse nervous system effects (eg, headache, dizziness) and GI effects (eg, constipation, diarrhea) occur most frequently during famotidine therapy. Although adverse effects of the drug generally are not severe, discontinuance of famotidine therapy has been necessary in up to 14% of patients. Adverse effects generally are similar when famotidine is administered orally or IV.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2151


Fever, hypertension, flushing, musculoskeletal pain, arthralgia, and tinnitus have been reported in 1% or less of patients receiving famotidine, but a causal relationship to the drug has not been established in many cases. An acute episode of gout occurred in one patient during therapy with the drug.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2151


Leukocytosis, leukopenia, neutropenia, pancytopenia, agranulocytosis, eosinophilia, prolonged erythrocyte sedimentation rate (ESR), and thrombocytopenia have occurred rarely in patients receiving famotidine. Changes in serum protein or cholesterol concentrations also have occurred.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2151


For more Drug Warnings (Complete) data for FAMOTIDINE (10 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Ulcer Agents

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)


Histamine H2 Antagonists

Drugs that selectively bind to but do not activate histamine H2 receptors, thereby blocking the actions of histamine. Their clinically most important action is the inhibition of acid secretion in the treatment of gastrointestinal ulcers. Smooth muscle may also be affected. Some drugs in this class have strong effects in the central nervous system, but these actions are not well understood. (See all compounds classified as Histamine H2 Antagonists.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
FAMOTIDINE
5.2.2 FDA UNII
5QZO15J2Z8
5.2.3 Pharmacological Classes
Histamine-2 Receptor Antagonist [EPC]; Histamine H2 Receptor Antagonists [MoA]
5.3 ATC Code

A - Alimentary tract and metabolism

A02 - Drugs for acid related disorders

A02B - Drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

A02BA - H2-receptor antagonists

A02BA03 - Famotidine


5.4 Absorption, Distribution and Excretion

All H2-receptor antagonists are distributed in breast milk and cerebral spinal fluid. /Histamine H2-receptor antagonists/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 1612


Distribution of famotidine into human body tissues and fluids has not been fully characterized. The apparent volume of distribution of the drug is reported to be 1.1-1.4 l/kg in adults and does not appear to be altered substantially in patients with renal dysfunction. Following oral or IV administration in rats, famotidine is widely distributed, appearing in highest concentrations in the kidney, liver, pancreas, and submandibular gland. The drug is 15-20% protein bound.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2149


In rats famotidine appears to distribute only minimally into the CNS, and does not cross the placenta. It is not known whether the drug crosses the placenta in humans. Famotidine is distributed into milk in rats; however, it is not known whether the drug is distributed into milk in humans.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2149


Famotidine is excreted principally in urine via glomerular filtration and tubular secretion. Approximately 25-30 or 65-80% of a dose is excreted unchanged in urine within 24 hours following oral or IV administration, respectively, and approximately 13-49 or 52-82% of a single 40 mg oral or IV dose respectively, is excreted within 72 hours. ... The remainder of an orally administered dose is eliminated in feces.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2149


For more Absorption, Distribution and Excretion (Complete) data for FAMOTIDINE (7 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Famotidine is metabolized in the liver to famotidine S-oxide (S-famotidine). The metabolite does not appear to inhibit gastric acid secretion. Orally administered famotidine undergoes minimal metabolism on first pass through the liver.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2149


5.6 Mechanism of Action

H2-receptor antagonists inhibit basal and nocturnal gastric acid secretion by competitive inhibition of the action of histamine at the histamine H2-receptors of the parietal cells. They also inhibit gastric acid secretion stimulated by food, betazole, pentagastrin, caffeine, insulin, and physiological vagal reflex. /Histamine H2-receptor antagonists/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 1612


Weak inhibitor of hepatic cytochrome p450 mixed function oxidase system.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 1612


Famotidine is a competitive H2 receptor antagonist that inhibits basal, overnight, and pentagastrin-stimulated gastric acid secretion. Pharmacologically, it is three times more potent than ranitidine and 20 times more potent than cimetidine.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 902