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Substance Name: Sirolimus [USAN:INN:BAN]
RN: 53123-88-9
UNII: W36ZG6FT64
InChIKey: QFJCIRLUMZQUOT-HPLJOQBZSA-N
Note
- A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.
Molecular Formula
- C51-H79-N-O13
Molecular Weight
- 914.1791
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibiotics, Antineoplastic
- Antifungal Agents
- Antineoplastic Agents
- Antiviral (COVID-19)
- Drug / Therapeutic Agent
- Immunologic Factors
- Immunosuppressant
- Immunosuppressive Agents
- Mutation Data
- Natural Product
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Names and Synonyms
Name of Substance
- Sirolimus
- Sirolimus [USAN:INN:BAN]
MeSH Heading
- Sirolimus
Synonyms
- (-)-Rapamycin
- (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-((1R)-2-((1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl)-1-methylethyl)-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido(2,1-C)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
- Antibiotic AY 22989
- AY 22989
- AY-22989
- CCRIS 9024
- Cypher
- DE-109
- EC 610-965-5
- HSDB 7284
- NSC 226080
- RAPA
- Rapammune
- Rapamune
- Rapamycin
- SILA 9268A
- Sirolimus
- Supralimus
- UNII-W36ZG6FT64
- Wy 090217
- WY-090217
Systematic Names
- (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-((1R)-2-((1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl)-1-methylethyl)-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido(2,1-C)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
- 23,27-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone, 9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-(3-(4-hydroxy-3-methoxycyclohexyl)-1-methylethyl)-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-, (3S-(3R*(S*(1R*,3S*,4S*)),6S*,7E,9S*,10S*,12S*,14R*,15E,17E,19E,21R*,23R*,26S*,27S*,34aR*))-
- Rapamycin
Registry Numbers
CAS Registry Number
- 53123-88-9
FDA UNII
- W36ZG6FT64
Other Registry Numbers
- 1179372-35-0
- 1189166-54-8
- 1233221-34-5
- 1353039-01-6
System Generated Number
- 0053123889
Structure Descriptors
InChI
InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1InChIKey
QFJCIRLUMZQUOT-HPLJOQBZSA-NSmiles
CO[C@@H]1C[C@H](C[C@@H](C)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 597mg/kg (597mg/kg) | Journal of Antibiotics. Vol. 31, Pg. 539, 1978. | |
mouse | LD50 | oral | > 2500mg/kg (2500mg/kg) | Journal of Antibiotics. Vol. 28, Pg. 721, 1975. | |
rat | LD50 | intraperitoneal | 18220ug/kg (18.22mg/kg) | National Technical Information Service. Vol. PB83-228577, |