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1-Methyl-1-nitroso-3-(3,4,5,6-tetrahydroxy-1-oxohexan-2-yl)urea

HCID 5299
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
18883-66-4
Standard SMILES
CN(N=O)C(=O)NC(C=O)C(O)C(O)C(O)CO
InChIKey
AGRCPNMCOXLKFO-UHFFFAOYSA-N
Molecular formula
C8H15N3O7
Average molar mass
265.22 g/mol
Monoisotopic mass
265.09099983

Overview

See also: Streptozocin (annotation moved to).

Names & identifiers

Preferred name
1-Methyl-1-nitroso-3-(3,4,5,6-tetrahydroxy-1-oxohexan-2-yl)urea
IUPAC
1-methyl-1-nitroso-3-(3,4,5,6-tetrahydroxy-1-oxohexan-2-yl)urea
English name
Streptozotocin
Molecular formula
C8H15N3O7
Molecular weight
265.22

Names & synonyms

NSC379172-Deoxy-2-(3-methyl-3-nitrosoureido)-.alpha.(and.beta.)-D-glucopyranose1-methyl-1-nitroso-3-(3,4,5,6-tetrahydroxy-1-oxohexan-2-yl)ureaAKOS024370866NCI60_041900ST51006815N-methyl-N-nitroso{[2-oxo-1-(1,2,3,4-tetrahydroxybutyl)ethyl]amino}carboxamideSTZSTREPTOZOCINSTRZANOSARStreptozotocin (STZ)
Show more names
Streptozotocin (U-9889)beta-dimethylacrylshikoninstrzU-9889Stzocin

Database identifiers

CAS
18883-66-4
PubChem CID
5299

Properties

Computed structural properties

XLogP
-3.2
Topological polar surface area
160 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
8
Rotatable bonds
6
Heavy atoms
18
Formal charge
0
Complexity
300

Physicochemical properties

Melting point
121 °C · 121 °C (dec.) (lit.)
alpha
25 · D25 +39°
Boiling point
408.44 °C · 408.44°C (rough estimate)
Density
1.441 · 1.4410 (rough estimate)
refractive index
1.65 · 1.6500 (estimate)
storage temp.
-20 °C · -20°C
solubility
Soluble in DMSO (up to 25 mg/ml) or in Water (up to 25 mg/ml)
form
powder
pka
1.3 · pKa 1.3 (Uncertain)
color
white to light yellow
Water Solubility
soluble
Sensitive
Hygroscopic
Merck
13 · 13,8912
BRN
2060675 · 2060675
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 month.
InChI

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
3-10-21
PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
LZ5775000
ridadr
3249
hs_code
29419090
Toxicity
LD50 in female mice (mg/kg): 360 i.p.; 275 i.v.; in male dogs (mg/kg): 50 i.v. (Iwasaki)
risk_code
40-61-46-45-22-20/21/22
Signal word
Warning
Symbol(GHS)
GHS02,GHS08
hazard_code
Xn,T
safety_code
36/37-53-45-36-22
hazard_class
6.1(b)
Storage Class
4.1B - Flammable solid hazardous materials
packing_group
III
Hazard statements
H228-H341-H351
Hazard Classifications
Carc. 2Flam. Sol. 1Muta. 2
Precautionary statements
P201-P202-P210-P240-P241-P308+P313
Hazardous Substances Data
18883-66-4(Hazardous Substances Data)

Chemistry & industry

Applications · 8 items

UsesIt is a compound containing N-nitroso ,it acts as a nitric oxide donor in pancreatic islets ; it can induce the death of diabetic animal model style of insulin-secreting cells . Efficient DNA methylation agent, can induce chromosome breakage.it has cell toxicity On the neuroendocrine tumor cell lines with the expression of GLUT2 glucose transporter (GLUT2 glucose transporter) . Streptozocin is used for inducing Type 1 diabetes in Medical researches .

DescriptionStreptozotocin (STZ) was originally identified in the late 1950s as an antibiotic and was discovered in a strain of the soil microbe Streptomyces achromogenes. In the mid-1960s, STZ was found to be selectively toxic to the beta cells of the pancreatic islets and thus it is used in animal model of diabetes and as a medical treatment for cancers of the beta cells. STZ’s use in cancer chemotherapy received Food and Drug Administration approval in July 1982 and the drug was subsequently marketed as Zanosar.

Usesantineoplastic, alkylating agent

UsesStreptozotocin is used in the treatment metastatic cancer of the pancreatic islet cells. Streptozotocin has a highlrisk of toxicity and is generally limited to cancers that are inoperable.

Usessomatostatin octapeptide analog

UsesStreptozotocin is an unusual aminoglycoside containing a nitrosoamino group produced by Streptomyces achromogenes and discovered in 1959 as an antibiotic. The nitrosoamino group enables the metabolite to act as a nitric oxide (NO) donor. NO is an important messenger molecule involved in many physiological and pathological processes in the body. Streptozotocin is also widely used to induce diabetes in rodent models by inhibition of β-cell O-GlcNAcase.

General DescriptionStreptozocin is available in 1-g vials for IV administrationin the treatment of metastatic islet cell carcinoma of the pancreas,colon cancer, and Hodgkin’s disease. Activation resultsin the formation of methyl carbonium ions, which alkylateDNA, but the agent is less effective in alkylating DNAand carbamylating proteins than other nitrosoureas, which isbecause in part of an intramolecular carbamoylation. The internalcarbamate group migration occurs via the hydroxylgroups of the glucose portion of the molecule. There is a reducedeffect on RNA function compared with other nitrosoureasas well. The hydrophilic agent is rapidly clearedfrom the plasma with an elimination half-life of 35 minutes.The presence of the glucose moiety allows for utilization ofglucose transporters, which concentrate the compound inthe -cells of the pancreas. The metabolism of the agent hasnot been well characterized. Renal toxicity is dose limitingand may present initially as proteinuria and azotemia butmay progress to renal failure. Nausea and vomiting may besevere with the agent, whereas myelosuppression is generallymild. Normal glucose metabolism may be altered sothat hypoglycemia or hyperglycemia may be seen. In someanimal species, streptozocin produces diabetes but muchmilder effects are seen in man.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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-FEQHFJGESA-N
SMILES
CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O
CAS DataBase Reference
18883 · 18883-66-4
NCI Dictionary of Cancer Terms
streptozocin
FDA UNII
5 W494URQ81 · 5W494URQ81
NCI Drug Dictionary
streptozocin
ATC code
1 AD04 · L01AD04
Proposition 65 List
Streptozotocin (Streptozocin)
IARC
2 B · 2B (Vol. 17, Sup 7) 1987
EPA Substance Registry System
Streptozotocin (18883-66-4)
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
2 · GHS02,GHS08
Signal word
Warning
Hazard statements
228 · H228-H341-H351
Precautionary statements
201 · P201-P202-P210-P240-P241-P308+P313
PPE
3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
Xn,T
Risk Statements
40 · 40-61-46-45-22-20/21/22
Safety Statements
36 · 36/37-53-45-36-22
RIDADR
3249 · 3249
WGK Germany
3 · 3
RTECS
5775000 · LZ5775000
F
3 · 3-10-21
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29419090 · 29419090
Storage Class
4.1 B · 4.1B - Flammable solid hazardous materials
Hazard Classifications
2 Flam · Carc. 2Flam. Sol. 1Muta. 2
Hazardous Substances Data
18883 · 18883-66-4(Hazardous Substances Data)
Toxicity
50 in · LD50 in female mice (mg/kg): 360 i.p.; 275 i.v.; in male dogs (mg/kg): 50 i.v. (Iwasaki)

General DescriptionOff-white powder. Melting point 115°C. Used as an anti-cancer drug. Carcinogenic.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
上海乾豪生物科技有限公司13524877553 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
诺达多糖(大连)医药科技有限公司13840935583 13840935583 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Syntechem Co.,Ltd[email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
武汉瑞立升科技发展有限公司27-027-83314682 13554138826 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
南京美博生物科技有限公司025-58619198 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
Abblis Chemicals LLC+1-832-373-8299 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都宇洋高科技发展有限责任公司+86-28-61777709 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
北京清露源科技有限公司+86 (10) 6333-0989 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
上海汇凯化学科技有限公司021-61995394 18916691159 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
安倍医疗器械贸易(上海)有限公司400-1500-680 021-62402299 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
上海宝曼生物科技有限公司021-62130998 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
上海泽涵生物医药科技有限公司021-61350663 13052117465 · [email protected]

Additional notes

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