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Substance Name: Tacrolimus [USAN:INN:BAN]
RN: 109581-93-3
UNII: WM0HAQ4WNM
InChIKey: NWJQLQGQZSIBAF-MLAUYUEBSA-N
Note
- A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.
Molecular Formula
- C44-H69-N-O12.H2-O
Molecular Weight
- 822.0389
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Formulas
- Structure Descriptors
- Toxicity
Classification Codes
- Antiviral (COVID-19)
- Calcineurin Inhibitors
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Immunologic Factors
- Immunosuppressant
- Immunosuppressive Agents
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Names and Synonyms
Name of Substance
- Tacrolimus
- Tacrolimus [USAN:INN:BAN]
MeSH Heading
- Tacrolimus
Synonyms
- (-)-(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-allyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-Hexadecahydro-5,19-dihydroxy-3-((E)-2-((1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone)monohydrate
- 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, monohydrate, (3S-(3R*,(E(1S*,3S*,4S*)),4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*))-
- Astagraf XL
- FK 506
- FR 900506
- FR900506
- LCP-Tacro
- NSC 758659
- Prograf
- Protopic
- Tacrolimus
- Tacrolimus hydrate
- Tsukubaenolide hydrate
- UNII-WM0HAQ4WNM
Systematic Name
- 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, monohydrate, (3S-(3R*,(E(1S*,3S*,4S*)),4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*))-
Registry Numbers
CAS Registry Number
- 109581-93-3
FDA UNII
- WM0HAQ4WNM
Related Registry Number
- 104987-11-3 (Parent)
System Generated Number
- 0109581933
Molecular Formulas
Molecular Formula
- C44-H69-N-O12.H2-O
Molecular Formula Fragments
- C44-H69-N-O12
- COMPONENT
- H2-O
Structure Descriptors
InChI
InChI=1S/C44H69NO12.H2O/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7;/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3;1H2/b25-19+,27-21+;/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+;/m0./s1InChIKey
NWJQLQGQZSIBAF-MLAUYUEBSA-NSmiles
O.CO[C@@H]1C[C@@H](CC[C@H]1O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | intravenous | 23600ug/kg (23.6mg/kg) | Drugs in Japan Vol. -, Pg. 720, 1995. | |
rat | LD50 | oral | 134mg/kg (134mg/kg) | Drugs in Japan Vol. -, Pg. 720, 1995. |