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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
  • Drug / Therapeutic Agent
  • Immunologic Factors
  • Immunosuppressant
  • Immunosuppressive Agents
  • Mutation Data
  • Natural Product

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

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/s1

InChIKey

QFJCIRLUMZQUOT-HPLJOQBZSA-N

Smiles

CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(/C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(/C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC)CC[C@H]1O

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,