CAS 18883-66-4|STREPTOZOTOCIN|3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea|STRZ|Streptozoticin|STZ|Streptozocin [Usan:Inn]|Streptozocinium [Latin]|Streptoz...

General Information

Structure

Molecular Formula

C₈H₁₅N₃O₇

Molecular Mass

265.2206

Exact Mass

265.09099984

Charge

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

InChIKey

ZSJLQEPLLKMAKR-GKHCUFPYSA-N

Canonic Smiles

OC[C@H]1O[C@H](O)[C@@H]([C@H]([C@@H]1O)O)NC(=O)N(N=O)C

Isomeric Smiles

O1[C@@H]([C@@H](O)[C@H](O)[C@@H](NC(=O)N(N=O)C)[C@H]1O)CO

Calculated Properties

JChem

Acid pKa

11.425146

H Acceptors

H Donor

LogD (pH = 5.5)

-2.7202861

LogD (pH = 7.4)

-2.7203243

Log P

-2.7202857

Molar Refractivity

55.9552

Polarizability

21.796125

Polar Surface Area

151.92

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

-1.71

LOG S

-0.9

Solubility (Water)

3.35e+01 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

STREPTOZOTOCINSTRZStreptozoticinSTZStreptozocin [Usan:Inn]Streptozocinium [Latin]Streptozocinum [INN-Latin]Streptozocine [INN-French]Zanosar

IUPAC name

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

Synonyms

StreptozocinStreptozotocinStreptozocinZanosarN-(Methylnitrosocarbamoyl)-α-D-glucosamine StreptozocinSTZ

IUPAC Traditional name

streptozocin

Names and Identifiers

Registration numbers

PubChem SID

1609637742489942846508872

PubChem CID

CAS Number

EC Number

Beilstein Number

MDL Number

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-1.7

Solubility

5070 mg/L

Apperance

white to off-white powder

Melting Point

121 °C (dec.)(lit.)

Safety Information

-20°C

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00428

Drug Groups

approved

Description

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

Indication

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

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.

Toxicity

Symptoms of overdose include nausea and vomiting, anorexia, myelosuppression; and nephrotoxicity.

Affected Organisms

Humans and other mammals

Biotransformation

Primarily hepatic

Absorption

Poor oral absorption (17-25%)

Half Life

5-15 minutes

Elimination

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

References

• [Link]

• Brentjens R, Saltz L: Islet cell tumors of the pancreas: the medical oncologist's perspective. Surg Clin North Am. 2001 Jun;81(3):527-42. [Pubmed]

• Wang Z, Gleichmann H: GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes. 1998 Jan;47(1):50-6. [Pubmed]

• Schnedl WJ, Ferber S, Johnson JH, Newgard CB: STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43(11):1326-33. [Pubmed]

• VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. [Pubmed]

• Mansford KR, Opie L: Comparison of metabolic abnormalities in diabetes mellitus induced by streptozotocin or by alloxan. Lancet. 1968 Mar 30;1(7544):670-1. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. Pubmed

• Wang Z, Gleichmann H: GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes. 1998 Jan;47(1):50-6. Pubmed

• Mansford KR, Opie L: Comparison of metabolic abnormalities in diabetes mellitus induced by streptozotocin or by alloxan. Lancet. 1968 Mar 30;1(7544):670-1. Pubmed

• Schnedl WJ, Ferber S, Johnson JH, Newgard CB: STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43(11):1326-33. Pubmed

• Link

• Brentjens R, Saltz L: Islet cell tumors of the pancreas: the medical oncologist's perspective. Surg Clin North Am. 2001 Jun;81(3):527-42. Pubmed

• http://www.rxlist.com/zanosar-drug.htm

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Brand Name

STREPTOZOTOCINSTRZStreptozoticinSTZStreptozocin [Usan:Inn]Streptozocinium [Latin]Streptozocinum [INN-Latin]Streptozocine [INN-French]Zanosar

IUPAC name

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

Synonyms

StreptozocinStreptozotocinStreptozocinZanosarN-(Methylnitrosocarbamoyl)-α-D-glucosamine StreptozocinSTZ

IUPAC Traditional name

streptozocin

Registration numbers

PubChem SID

1609637742489942846508872

PubChem CID

CAS Number

EC Number

Beilstein Number

MDL Number

References

PubChem Literature

From Data Sources

• VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. Pubmed

• Wang Z, Gleichmann H: GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes. 1998 Jan;47(1):50-6. Pubmed

• Mansford KR, Opie L: Comparison of metabolic abnormalities in diabetes mellitus induced by streptozotocin or by alloxan. Lancet. 1968 Mar 30;1(7544):670-1. Pubmed

• Schnedl WJ, Ferber S, Johnson JH, Newgard CB: STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43(11):1326-33. Pubmed

• Link

• Brentjens R, Saltz L: Islet cell tumors of the pancreas: the medical oncologist's perspective. Surg Clin North Am. 2001 Jun;81(3):527-42. Pubmed

• http://www.rxlist.com/zanosar-drug.htm

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

-1.7

Solubility

5070 mg/L

Apperance

white to off-white powder

Melting Point

121 °C (dec.)(lit.)

Safety Information

-20°C

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

Molecule Details

DrugBank

DB00428

Drug Groups

approved

Description

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

Indication

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

Pharmacology

Toxicity

Symptoms of overdose include nausea and vomiting, anorexia, myelosuppression; and nephrotoxicity.

Affected Organisms

Humans and other mammals

Biotransformation

Primarily hepatic

Absorption

Poor oral absorption (17-25%)

Half Life

5-15 minutes

Elimination

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

References

• [Link]

• Brentjens R, Saltz L: Islet cell tumors of the pancreas: the medical oncologist's perspective. Surg Clin North Am. 2001 Jun;81(3):527-42. [Pubmed]

• Wang Z, Gleichmann H: GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes. 1998 Jan;47(1):50-6. [Pubmed]

• Schnedl WJ, Ferber S, Johnson JH, Newgard CB: STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43(11):1326-33. [Pubmed]

• VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. [Pubmed]

• Mansford KR, Opie L: Comparison of metabolic abnormalities in diabetes mellitus induced by streptozotocin or by alloxan. Lancet. 1968 Mar 30;1(7544):670-1. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule

ID:311