ContaminantDB: Streptozocin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:53 UTC

Update Date

2026-03-31 20:20:40 UTC

Accession Number

CHEM002193

Identification

Common Name

Streptozocin

Class

Small Molecule

Description

Streptozocin is only found in individuals that have used or taken this drug.It is an antibiotic that is produced by Stretomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals. [PubChem]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.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
IARC Carcinogens Group 2B
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Antibiotic
Antibiotic, Antineoplastic
Antineoplastic Agent
Drug
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Deoxy-2-(((methylnitrosoamino)carbonyl)amino)-D-glucopyranose	ChEBI
2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose	ChEBI
Estreptozocina	ChEBI
N-D-Glucosyl-(2)-n'-nitrosomethylharnstoff	ChEBI
N-D-Glucosyl-(2)-n'-nitrosomethylurea	ChEBI
Streptozocine	ChEBI
Streptozocinium	ChEBI
Streptozocinum	ChEBI
Streptozotocin	ChEBI
Zanosar	ChEBI
Streptozotocine	HMDB
Teva brand OF streptozocin	HMDB
Streptozocin teva brand	HMDB
2-Deoxy-2-((methylnitrosoamino)carbonyl)amino-D-glucose	HMDB

Chemical Formula

C₈H₁₅N₃O₇

Average Molecular Mass

265.221 g/mol

Monoisotopic Mass

265.091 g/mol

CAS Registry Number

18883-66-4

IUPAC Name

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

Traditional Name

streptozocin

SMILES

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

InChI Identifier

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

InChI Key

ZSJLQEPLLKMAKR-GKHCUFPYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
N-methylnitrosourea
Nitrosourea
Oxane
Nitrosamide
Semicarbazide
Organic n-nitroso compound
Hemiacetal
Carbonic acid derivative
Secondary alcohol
Organic nitroso compound
Oxacycle
Polyol
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-nitrosoureas (CHEBI:9288 )
N-acylglucosamine (CHEBI:9288 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

DNA synthesis inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	115°C
Boiling Point	Not Available
Solubility	5070 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	33.5 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.7	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	11.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	151.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.96 m³·mol⁻¹	ChemAxon
Polarizability	23.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02mj-5940000000-8fb8f1885498bea8bc01	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-000i-5384590000-954f20357dc689aab130	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066s-1390000000-8a52d6755935e91be345	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9730000000-8e7df34a65b316df695e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9800000000-8768229ecc0345cd843a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9340000000-9e14b4f8a6d8f44c6ad6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9220000000-2ac584cea0c0d26bc11f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9200000000-dd74fa78262e5a7d35e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-4940000000-29bcfe413e3e5b2dd305	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0536-9100000000-2a734221e4d6f4a10693	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-722b10d68ba035f6a8c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-1090000000-4646c5accac0f8935a29	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-d7d9d98474284352116c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9300000000-9cad9495adf263c410f9	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Intravenous. Poor oral absorption (17-25%).

Mechanism of Toxicity

Streptozotocin is a naturally occurring chemical that is particularly toxic to the insulin-producing beta cells of the pancreas. It is used in medical research to produce an animal model for Type 1 diabetes in large dose as well as Type 2 diabetes with multiple low doses. Streptozotocin is similar enough to glucose to be transported into the cell by the glucose transport protein GLUT2, but is not recognized by the other glucose transporters. This explains its relative toxicity to beta cells, since these cells have relatively high levels of GLUT2. Streptozotocin is a glucosamine-nitrosourea (i.e. alkylating) compound. As with other alkylating agents in the nitrosourea class, it is toxic to cells by causing damage to the DNA, though other mechanisms may also contribute.

Metabolism

Primarily hepatic 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. Half Life: 5-15 minutes

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (6)

Uses/Sources

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

Minimum Risk Level

Not Available

Health Effects

Antibiotic resistance