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Streptozocin

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Also known as: Streptozotocin, 18883-66-4, Streptozosin, Estreptozocina, Streptozocine, Streptozocinium

Molecular Formula

C₈H₁₅N₃O₇

Molecular Weight

265.22 g/mol

InChI Key

ZSJLQEPLLKMAKR-GKHCUFPYSA-N

FDA UNII

8H27GUR065

An antibiotic that is produced by Stretomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals.

1 2D Structure

Streptozocin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea

2.1.2 InChI

InChI=1S/C8H15N3O7/c1-11(10-17)8(16)9-4-6(14)5(13)3(2-12)18-7(4)15/h3-7,12-15H,2H2,1H3,(H,9,16)/t3-,4-,5-,6-,7+/m1/s1

2.1.3 InChI Key

ZSJLQEPLLKMAKR-GKHCUFPYSA-N

2.1.4 Canonical SMILES

CN(C(=O)NC1C(C(C(OC1O)CO)O)O)N=O

2.1.5 Isomeric SMILES

CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O)N=O

2.2 Other Identifiers

2.2.1 UNII

8H27GUR065

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-deoxy-2-((methylnitrosoamino)carbonyl)amino-d-glucose

2. Streptozotocin

3. Streptozotocine

4. Zanosar

2.3.2 Depositor-Supplied Synonyms

1. Streptozotocin

2. 18883-66-4

3. Streptozosin

4. Estreptozocina

5. Streptozocine

6. Streptozocinium

7. Streptozocinum

8. 66395-18-4

9. 2-desoxy-2-(3-methyl-3-nitrosoureido)-d-glucopyranose

10. N-d-glucosyl-(2)-n'-nitrosomethylurea

11. Alpha-streptozocin

12. Streptozotocin (stz)

13. N-d-glucosyl-(2)-n'-nitrosomethylharnstoff

14. 2-deoxy-2-(((methylnitrosoamino)carbonyl)amino)-d-glucopyranose

15. Chebi:9288

16. Stz

17. 8h27gur065

18. Alkylating Agent

19. Dsstox_cid_1282

20. Dsstox_rid_76055

21. Dsstox_gsid_21282

22. C8h15n3o7

23. Mfcd00006607

24. Binds To Dna

25. 3-methyl-3-nitroso-1-[(2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea

26. Zanosar (tn)

27. Sr-05000001720

28. 2-deoxy-2-[[(methylnitrosoamino)carbonyl]amino]-d-glucose

29. 2-deoxy-2-({[methyl(nitroso)amino]carbonyl}amino)-alpha-d-glucopyranose

30. Ncgc00016738-01

31. Cas-18883-66-4

32. Spectrum_000960

33. Streptozotocin - Zanosar

34. 2-deoxy-2-{[methyl(nitroso)carbamoyl]amino}-alpha-d-glucopyranose

35. Prestwick3_000732

36. Spectrum2_000062

37. Spectrum3_001087

38. Spectrum4_001244

39. Spectrum5_001047

40. Epitope Id:134282

41. Schembl4748

42. Streptozocin; Streptozotocin

43. .alpha.-streptozocin

44. Bspbio_000684

45. Bspbio_002734

46. Kbiogr_001768

47. Kbioss_001440

48. Mls004774123

49. Divk1c_000531

50. Spectrum1500543

51. Unii-8h27gur065

52. Spbio_000243

53. Bpbio1_000754

54. Streptozocin (jan/usan/inn)

55. Bcbcmap01_000142

56. Hms501k13

57. Kbio1_000531

58. Kbio2_001440

59. Kbio2_004008

60. Kbio2_006576

61. Kbio3_001954

62. Ninds_000531

63. Hms1921a07

64. Hms2092i09

65. Hms2097c06

66. Hms3714c06

67. Pharmakon1600-01500543

68. 2-deoxy-2[[(methylnitrosoamino)-carbonyl]amino]-d-glucopyranose

69. Act03364

70. Zinc3977737

71. Streptozocin, >=98.0% (hplc)

72. Tox21_110585

73. Tox21_201859

74. Tox21_302974

75. Ccg-39870

76. Nsc757321

77. S1312

78. Akos025310730

79. Tox21_110585_1

80. Db00428

81. Nsc-757321

82. Idi1_000531

83. Smp1_000282

84. Ncgc00178500-01

85. Ncgc00178500-02

86. Ncgc00178500-03

87. Ncgc00178500-04

88. Ncgc00178500-07

89. Ncgc00256594-01

90. Ncgc00259408-01

91. 1-methyl-1-nitroso-3-((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-3-yl)urea

92. Smr001233317

93. Sbi-0051517.p003

94. Ab00513906

95. Sw199198-2

96. C07313

97. D05932

98. Ab00052092-03

99. Ab00052092_04

100. Ab00052092_05

101. 883s664

102. A937380

103. N-(methylnitrosocarbamoyl)-a-d-glucosamine

104. Q257331

105. Sr-01000939745

106. Sr-01000939745-3

107. Sr-05000001720-1

108. Sr-05000001720-2

109. W-201687

110. Streptozocin, Vetec(tm) Reagent Grade, 98%, Powder

111. Streptozocin, >=75% Alpha-anomer Basis, >=98% (hplc), Powder

112. Alpha-d-glucopyranose, 2-deoxy-2-(((methylnitrosoamino)carbonyl)amino)-

113. Wurcs=2.0/1,1,0/[a2122h-1a_1-5_2*ncnn=o/4c/3=o]/1/

114. .alpha.-d-glucopyranose, 2-deoxy-2-(((methylnitrosoamino)carbonyl)amino)-

115. 1-methyl-1-nitroso-3-((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2h-pyran-3-yl)urea

116. 1-methyl-1-nitroso-3-[(2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]urea

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₈H₁₅N₃O₇
Molecular Weight	265.22 g/mol
XLogP3	-1.4
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Exact Mass	265.09099983 g/mol
Monoisotopic Mass	265.09099983 g/mol
Topological Polar Surface Area	152 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	315
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
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	Zanosar
PubMed Health	Streptozocin (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	Each vial of ZANOSAR contains 1 g of the active ingredient streptozocin 2-deoxy-2 [[(methylnitrosoamino)carbonyl]amino]- (and )-D-glucopyranose and 220 mg citric acid anhydrous. ZANOSAR is available as a sterile, pale yellow, freeze-dried prepara...
Active Ingredient	Streptozocin
Dosage Form	Injectable
Route	Injection
Strength	1gm/vial
Market Status	Prescription
Company	Teva Pharms Usa

2 of 2
Drug Name	Zanosar
PubMed Health	Streptozocin (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	Each vial of ZANOSAR contains 1 g of the active ingredient streptozocin 2-deoxy-2 [[(methylnitrosoamino)carbonyl]amino]- (and )-D-glucopyranose and 220 mg citric acid anhydrous. ZANOSAR is available as a sterile, pale yellow, freeze-dried prepara...
Active Ingredient	Streptozocin
Dosage Form	Injectable
Route	Injection
Strength	1gm/vial
Market Status	Prescription
Company	Teva Pharms Usa

4.2 Therapeutic Uses

Antibiotics, Aminoglycoside; Antibiotics, Antineoplastic

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

... A SPECIFIC BETA CELL TOXIN & THEREFORE USEFUL IN TREATMENT OF METASTATIC ISLET CELL TUMORS.

American Medical Association, Department of Drugs. Drug Evaluations. 6th ed. Chicago, Ill: American Medical Association, 1986., p. 1191

IT HAS ... BEEN FOUND TO BE ACTIVE IN HODGKIN'S DISEASE, OTHER LYMPHOMAS, & OCCASIONALLY IN MELANOMA & MALIGNANT CARCINOID TUMORS ... .

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1222

THE PROFUSE WATERY DIARRHEA OBSERVED IN PATIENTS WITH PANCREATIC CHOLERA (VERNER MORRISON SYNDROME, SECRETORY DIARRHEA) PRODUCED BY METASTATIC NONBETA CELL TUMORS HAS BEEN RELIEVED BY INFUSION OF STREPTOZOCIN INTO THE HEPATIC ARTERY.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 964

MEDICATION (VET): ... EMPLOYED AS DIABETOGENIC AGENT IN EXPERIMENTAL ANIMALS.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1269

4.3 Drug Warning

PATIENTS WITH PRE-EXISTING IMPAIRED RENAL FUNCTION SHOULD NOT RECEIVE STREPTOZOTOCIN.

American Medical Association, Department of Drugs. Drug Evaluations. 6th ed. Chicago, Ill: American Medical Association, 1986., p. 1191

STREPTOZOTOCIN FREQUENTLY ASSOCIATED WITH CHANGES IN LIVER SCAN. SUGGESTED THAT MINOR SCAN CHANGES MIGHT BE ATTRIBUTED ERRONEOUSLY TO INTRINSIC HEPATIC DISEASE.

PMID:7356745 KAPLAN ET AL; J NUCL MED 21 (JAN): 84 (1980)

4.4 Drug Indication

For the treatment of malignant neoplasms of pancreas (metastatic islet cell carcinoma).

5 Pharmacology and Biochemistry

5.1 Pharmacology

Streptozocin is an antitumour antibiotic consisting of a nitrosourea moiety interposed between a methyl group and a glucosamine. Streptozocin is indicated in the treatment of metastatic islet cell carcinoma of the pancreas. Streptozocin inhibits DNA synthesis in bacterial and mammalian cells. In bacterial cells, a specific interaction with cytosine moieties leads to degradation of DNA. The biochemical mechanism leading to mammalian cell death has not been definitely established; streptozocin inhibits cell proliferation at a considerably lower level than that needed to inhibit precursor incorporation into DNA or to inhibit several of the enzymes involved in DNA synthesis. Although streptozocin inhibits the progression of cells into mitosis, no specific phase of the cell cycle is particularly sensitive to its lethal effects.

5.2 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Alkylating Drug [EPC]; Alkylating Activity [MoA]

5.4 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01A - Alkylating agents

L01AD - Nitrosoureas

L01AD04 - Streptozocin

5.5 Absorption, Distribution and Excretion

Absorption

Poor oral absorption (17-25%)

Route of Elimination

As much as 20% of the drug (or metabolites containing an N-nitrosourea group) is metabolized and/or excreted by the kidney.

IN ALL THESE SPECIES /MICE, RATS, CATS, MONKEYS & DOGS/ STR /STREPTOZOTOCIN/ GIVEN PARENTERALLY ... MARKEDLY CONCENTRATED IN LIVER & KIDNEY; FOR EXAMPLE, IN DOGS ... RETAINED IN LIVER FOR MANY HR AFTER ... NO LONGER ... DETECTED IN BLOOD .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V4 224

STREPTOZOTOCIN ... WELL ABSORBED FROM GI TRACT IN MICE, BUT ABSORPTION WAS POOR IN MONKEYS & NEGLIGIBLE IN DOGS.

(14)C-LABELLED STREPTOZOTOCIN GIVEN BY IV INJECTION WAS RAPIDLY CLEARED FROM BLOOD OF RATS, SO THAT LESS THAN 1% REMAINED AFTER 10 MINUTES.

STREPTOZOTOCIN (NSC-85998) WAS RAPIDLY EXCRETED IN URINE OF TREATED MICE; 72% OF AN INJECTED DOSE IN THE 4-HR URINE. FIVE URINARY METABOLITES WERE DETECTED ... .

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 151

Following intraperitoneal or IV administration of streptozocin in animals, the drug and its metabolites are rapidly distributed mainly into the liver, kidneys, intestine, and pancreas, with lower concentrations being distributed into skeletal muscle, spleen, lungs, heart, and thymus. Concentrations of the drug or its metabolites in the liver, kidneys, intestine, and pancreas are consistently higher than those in plasma. Streptozocin does not appear to cross the blood-brain barrier in animals or humans; however, in humans, metabolites of streptozocin readily distribute into CSF. ... The drug readily crosses the placenta in monkeys.

McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 547

5.6 Metabolism/Metabolites

Primarily hepatic

STUDIES WITH STREPTOZOTOCIN LABELLED WITH (14)C IN DIFFERENT POSITIONS INDICATE THAT ITS RAPID METABOLISM IN RAT ... RESULTS IN METABOLITE DERIVED FROM METHYL BEARING NITROSOUREIDO SIDECHAIN. /SRP: DIAZOMETHANE/

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. 380

/IN MICE URINE/ FIVE URINARY METABOLITES WERE DETECTED; 2 OF THEM WERE THE ALPHA AND BETA-ANOMERS OF THE ANTIBIOTIC.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 151

Streptozocin and metabolites have a short distribution phase (t1/2 6 min) followed by possibly two elimination phases representing active metabolites (t1/2 beta 3.5 hr, t1/2 gamma 40 hr).

Knoben, J.E. and P.O. Anderson (eds.) Handbook of Clinical Drug Data. 6th ed. Bethesda, MD: Drug Intelligence Publications, Inc. 1988., p. 425

Streptozocin is not orally active. After intravenous administration, it is rapidly cleared from plasma and is undetectable after three hours. Metabolites are detected in plasma for up to 24 hours. The drug concentrates in certain tissues; the liver and kidneys contain the highest levels, and pancreas also concentrates streptozocin. Parent drug and metabolites are eliminated rapidly by the kidney; 60% to 70% of a dose is recovered in urine within four hours. Only 10% to 20% of an excreted dose is parent drug.

American Medical Association, Department of Drugs. Drug Evaluations. 6th ed. Chicago, Ill: American Medical Association, 1986., p. 1191

5.7 Biological Half-Life

5-15 minutes

AFTER IV INFUSIONS OF 200-1600 MG/SQ M, PEAK CONCN IN PLASMA ARE 30-40 UG/ML; HALF-LIFE OF DRUG IS APPROX 15 MIN. ONLY 10-20% OF DOSE IS RECOVERED IN URINE.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1222

... STREPTOZOTOCIN ... FOLLOW APPARENT TWO-COMPARTMENT MODEL KINETICS IN MAN AFTER BOLUS IV INJECTION, WITH MEAN FAST & SLOW DISPOSITION HALF-TIME VALUES OF 4.6 & 40 MIN RESPECTIVELY. THE LATTER VALUE IS 2.5-FOLD GREATER THAN REPORTED PREVIOUSLY FOR PT RECEIVING STREPTOZOTOCIN BY SLOW IV INFUSION.

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. 80

SEVEN PATIENTS GIVEN SINGLE 1.5 G/SQ M IV DOSE SHOWED MEAN HALF-LIFE OF APPROX 40 MINUTES & HALF-LIFE OF ELIMINATION OF ABOUT 15 MINUTES.

PMID:142097 ADOLPHE ET AL; J CLIN PHARMACOL 17 (JUL): 379 (1977)

5.8 Mechanism of Action

Although its mechanism of action is not completely clear, streptozocin is known to inhibit DNA synthesis, interfere with biochemical reactions of NAD and NADH, and inhibit some enzymes involved in gluconeogenesis. Its activity appears to occur as a result of formation of methylcarbonium ions, which alkylate or bind with many intracellular molecular structures including nucleic acids. Its cytotoxic action is probably due to cross-linking of strands of DNA, resulting in inhibition of DNA synthesis.

DRUG IS CAPABLE OF INHIBITING SYNTH OF DNA IN MICROORGANISMS & MAMMALIAN CELLS; IT AFFECTS ALL STAGES OF MAMMALIAN CELL CYCLE. BIOCHEMICAL STUDIES HAVE ALSO REVEALED POTENT INHIBITORY EFFECTS ON PYRIDINE NUCLEOTIDES & ON KEY ENZYMES INVOLVED IN GLYCONEOGENESIS.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1271

Mechanisms underlying cytotoxicity by the monofunctional nitrosourea streptozotocin were evaluated in DNA repair-deficient E coli mutants. Strains not proficient in recombinational repair which lack either RecA protein or RecBC gene products were highly sensitive to streptozotocin (1X10-4 to 1X10-6 M concn for 30 min at 37 C). In contrast, cells that constituitively synthesize RecA protein and cannot initiate SOS repair mechanisms because of uncleavable LexA repressor (recAo98 lexA3) were resistant to this drug compared to a lexA3 strain. E coli cells lacking both 3-methyladenine DNA glycosylases I (tag) and II (alkA) also were highly sensitive to streptozotocin. DNA synthesis was most inhibited by streptozotocin in recA and alkA tag E coli mutants, but was suppressed less markedly in wild-type and recBC cells. DNA degradation was most extensive in recA E coli after streptozotocin treatment (400 ul 10-3 M for 30 min at 37 C), while comparable in recBC, alkA tag, and wild-type cells. Although incr single-stranded DNA breaks were present after streptozotocin treatment in recA and recBC mutants compared to the wild type, no significant incr in DNA single-stranded breaks was noted in alkA tag E coli. Further, DNA breaks in recBC cells were repaired, while those present in recA cells were not.

PMID:2475773 Fram RJ et al; Mutat Res 218 (2): 125-33 (1989)

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