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Rapamycin(CAS No. 53123-88-9)

Rapamycin C51H79NO13 (cas 53123-88-9) Molecular Structure

53123-88-9 Structure

Identification and Related Records

【Name】
Rapamycin
【CAS Registry number】
53123-88-9
【Synonyms】
Stereoisomer of 9,10,12,13,14,21,22,23,24,25,26,27,32,33,34, 34a-hexadecahydro-9,27-dihydroxy-3-[2-(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
RAP
Sirolimus [USAN:BAN:INN]
23,27-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29
AY 22989
Rapamycin (TN)
RPM
23,27-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone,
(6H,31H)-pentone, 4,9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-
3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
Antibiotic AY 22989
AY-22989
23,27-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine
9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-
-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-,
Siroliums(Rapamycin)
Sirolimus (Rapamycin)
Rapamycin(Sirolimus)
Sirolimus[USAN:BAN:INN]
【Molecular Formula】
C51H79NO13 (Products with the same molecular formula)
【Molecular Weight】
914.17186
【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/s1
【InChIKey】
QFJCIRLUMZQUOT-HPLJOQBZSA-N
【Canonical SMILES】
CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
【Isomers smiles】
C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C
(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C
[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC
【MOL File】
53123-88-9.mol

Chemical and Physical Properties

【Appearance】
yellow solid
【Density】
1.182 g/cm3
【Melting Point】
183-185 oC
【Boiling Point】
973.017 oC at 760 mmHg
【Refractive Index】
1.55
【Flash Point】
542.261 oC
【Water】
Soluble in DMSO and Methanol
【Solubilities】
Soluble in DMSO and Methanol
【Color/Form】
Colorless crystalline solid from ether
【Stability】
Stable if stored as directed.
【Storage temp】
-20°C
【Spectral properties】
UV max (95 percent ethanol): 267, 277, 288 nm (the absorbance of a solution containing one gram per 100 ml contained in a cell having an absorption path of one cm: 417, 541, and 416)
Specific optical rotation at 25 deg C for D (sodium) line = -58.2 deg (methanol)
【Computed Properties】
Molecular Weight:914.17186 [g/mol]
Molecular Formula:C51H79NO13
XLogP3-AA:6
H-Bond Donor:3
H-Bond Acceptor:13
Rotatable Bond Count:6
Tautomer Count:15
Exact Mass:913.555142
MonoIsotopic Mass:913.555142
Topological Polar Surface Area:195
Heavy Atom Count:65
Formal Charge:0
Complexity:1760
Isotope Atom Count:0
Defined Atom Stereocenter Count:15
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:4
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
R36/38
【Safety Statements 】
S22;S24/25
【Safety】

Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:?IrritantXi
Risk Statements: 36/38?
R36/38:Irritating to eyes and skin.
Safety Statements: 22-24/25-37/39-26?
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.?
S37/39:Wear suitable gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RTECS of Rapamycin (CAS NO.53123-88-9): VE6250000

【Sensitive】
Moisture Sensitive/Light Sensitive/Hygroscopic
【Formulations/Preparations】
Rapamune
Rapamycin
Oral: Solution 1mg/mL Rapamune (Wyeth). Tablets: 1 mg Rapamune (with povidone), (Wyeth); 2 mg Rapamune (with Povidone), (Wyeth).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl sirolimus, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

? Rapamycin (CAS NO.53123-88-9), its Synonyms are 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*))- ; Sirolimus ; Rapammune ; Rapamune . It is white to off-white solid.

【Octanol/Water Partition Coefficient】
log Kow = 4.81 /Estimated/
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Triene macrolide antibiotic isolated from Streptomyces hygroscopicus.
【Usage】

Used as an immunosuppressant

Biomedical Effects and Toxicity

【Biological Activity】
Antifungal and immunosuppressant. Specific inhibitor of mTOR (mammalian target of Rapamycin). Complexes with FKBP-12 and binds mTOR inhibiting its activity. Inhibits interleukin-2-induced phosphorylation and activation of p70 S6 kinase.
【Pharmacological Action】
- Substances that reduce the growth or reproduction of BACTERIA.
- Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
- Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
- Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
【Therapeutic Uses】
Sirolimus is indicated for the prevention of rejection of transplanted kidney allografts. It is recommended that sirolimus be used in a regimen with cyclosporine and corticosteroids. /Included in US product labeling/
Long-term results after percutaneous coronary intervention in the treatment of chronic total coronary occlusions is hindered by a significant rate of restenosis and reocclusion. In the treatment of relatively simple nonocclusive lesions, sirolimus-eluting stents have shown dramatically reduced restenosis rates compared with bare metal stents, but whether these results are more widely applicable is unknown. ... The use of sirolimus-eluting stents in the treatment of chronic total coronary occlusions is associated with a reduction in the rate of major adverse cardiac events and restenosis compared with bare metal stents. [Hoye A et al; J Am Coll Cardiol 43 (11): 1954-8 (2004)]
【Biomedical Effects and Toxicity】
Following administration of /Sirolimus/ Oral Solution, sirolimus is rapidly absorbed, with a mean time-to-peak concentration (t max ) of approximately 1 hour after a single dose in healthy subjects and approximately 2 hours after multiple oral doses in renal transplant recipients. The systemic availability of sirolimus was estimated to be approximately 14% after the administration of /Sirolimus/ Oral Solution. The mean bioavailability of sirolimus after administration of the tablet is about 27% higher relative to the oral solution.
In 22 healthy volunteers receiving Rapamune Oral Solution, a high-fat meal altered the bioavailability characteristics of sirolimus. Compared with fasting, a 34% decrease in the peak blood sirolimus concentration (C max ), a 3.5-fold increase in the time-to-peak concentration (t max ), and a 35% increase in total exposure (AUC) was observed. After administration of Rapamune Tablets and a high-fat meal in 24 healthy volunteers, C max , t max , and AUC showed increases of 65%, 32%, and 23%, respectively.
Absorption: Rapid, from the gastrointestinal tract. Bioavailability is approximately 14%. Rate of absorption is decreased in the presence of a high-fat diet. The rate and extent of absorption is reduced in black patients.
The mean (? SD) blood-to-plasma ratio of sirolimus was 36 ? 17.9 in stable renal allograft recipients, indicating that sirolimus is extensively partitioned into formed blood elements. The mean volume of distribution of sirolimus is 12 ? 7.52 L/kg. Sirolimus is extensively bound (approximately 92%) to human plasma proteins. In man, the binding of sirolimus was shown mainly to be associated with serum albumin (97%), (alpha) 1 -acid glycoprotein, and lipoproteins.
Elimination: 57 to 63 hours. May be significantly increased (up to 72 hours) in males.
After a single dose of (14)C-sirolimus in healthy volunteers, the majority (91%) of radioactivity was recovered from the feces, and only a minor amount (2.2%) was excreted in urine.
It is not known whether sirolimus is distributed in human breast milk. However, trace amounts of sirolimus is excreted in the milk of lactating rats.

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