Structure via PubChem · Public domain (PubChem)
α-streptozocin
Sign in to saveAlso known as -nitrosomethylharnstoff, Zanosar, 2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose, Estreptozocina, Streptozotocin, Streptozocinium, N-D-Glucosyl-(2)-n'-nitrosomethylurea, 2-Deoxy-2-(((methylnitrosoamino)carbonyl)amino)-D-glucopyranose
Streptozotocin or streptozocin (INN, USP) (STZ) is a naturally occurring alkylating antineoplastic agent that is particularly toxic to the insulin-producing beta cells of the pancreas in mammals. It is used in medicine for treating certain cancers of the islets of Langerhans and used in medical research to produce an animal model for hyperglycemia and Alzheimer's in a large dose, as well as type 2 diabetes or type 1 diabetes with multiple low doses.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470471155
- Drug.IUPAC_name
- 2-Deoxy-2-({[methyl(nitroso)amino]carbonyl}amino)-β-D-glucopyranose
- Drug.image
- Streptozocin (Haworth).svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 160
- Drug.tradename
- Zanosar
- Drug.MedlinePlus
- a684053
- Drug.pregnancy_US
- D
- Drug.legal_status
- Rx-only
- Drug.routes_of_administration
- Intravenous
- Drug.bioavailability
- 17–25% (100% if IV)
- Drug.metabolism
- Liver, kidney
- Drug.elimination_half life
- 35–40 minutes
- Drug.CAS_number
- 18883-66-4
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- AD04
via Wikipedia infobox
Chemical data
- Formula
- C8H15N3O7
- Molecular weight
- 265.22 g/mol
- IUPAC name
- 1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
- SMILES
- CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O)N=O
- InChIKey
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N
- XLogP
- -1.4
- Polar surface area
- 152 Ų
- H-bond donors
- 5
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 265.091
Show 5 more facts
- chemical formula
- C₈H₁₅N₃O₇
- canonical SMILES
- CN(C(=O)NC1C(C(C(OC1O)CO)O)O)N=O
- isomeric SMILES
- CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O)N=O
- World Health Organisation international non-proprietary name
- streptozocin
- Commons category
- Streptozocin
via Wikidata · CC0
~6 min read
Article
7 sectionsContents
- Usage
- Mechanism
- History
- Biosynthesis
- See also
- References
- External links
{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470471155 | IUPAC_name = 2-Deoxy-2-({[methyl(nitroso)amino]carbonyl}amino)-β-D-glucopyranose | image = Streptozocin (Haworth).svg | image_class = skin-invert-image | width = 160
| tradename = Zanosar | MedlinePlus = a684053 | pregnancy_US = D | legal_status = Rx-only | routes_of_administration = Intravenous