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Sirolimus (Rapamune) is structurally related to tacrolimus. It is approved for use as an adjunctive agent in combination with cyclosporine for prevention of acute renal allograft rejection. It blocks IL-2-dependent T-cell proliferation by inhibiting a cytoplasmic serine– threonine kinase. This mechanism of action is different from those of tacrolimus and cyclosporine. This allows sirolimus to augment the immunosuppressive effects of these drugs.
Rapamycin is an immunosuppressant that is used primarily to prevent the rejection of organ and bone marrow transplant. It was first described as a potent inhibitor of IL-2 activation of lymphocytes (IC50 = 5 pM). It is now known that rapamycin specifically interacts with the cytosolic FK-binding protein 12 (FKBP12) to form a complex which inhibits the mammalian target of rapamycin (mTOR) pathway by directly binding to mTOR Complex 1 (mTORC1). Rapamycin and other inhibitors of mTORC1 signaling show potential in treating cancer, adipogenesis, diabetes, tuberous sclerosis, and cardiovascular disease.[Cayman Chemical]
31-(trimethylsilylether)rapamycin
dimethylphosphinic acid chloride
Ridaforolimus
sirolimus
| Conditions | Yield |
|---|---|
|
31-(trimethylsilylether)rapamycin;
With
3,5-Lutidine;
In
dichloromethane;
at 0 - 5 ℃;
for 1.08333h;
Inert atmosphere;
dimethylphosphinic acid chloride;
In
dichloromethane;
at 0 - 5 ℃;
for 1h;
Inert atmosphere;
|
81.03 %Chromat. 5.14 %Chromat. |
C57H95NO13Si2
31,42-bis(trimethylsilylether)rapamycin
sirolimus
| Conditions | Yield |
|---|---|
|
C57H95NO13Si2; 31,42-bis(trimethylsilylether)rapamycin;
With
sulfuric acid; water;
In
acetone;
at 0 - 5 ℃;
for 0.166667h;
With
sodium hydrogencarbonate; acetic acid;
In
water; acetone;
at 0 - 15 ℃;
for 0.283333 - 0.416667h;
With
sodium acetate;
In
water; acetone;
at 20 ℃;
for 60.1667h;
pH=5 - 5.5;
Aqueous sodium acetate buffer;
|
87.6% |
The CAS number of Rapamycin is 53123-88-9.
More information of Rapamycin 53123-88-9 are:
|
CAS Number |
53123-88-9 |
|
Density |
1.182 g/cm3 |
|
Melting Point |
183-185 ºC |
|
Boiling Point |
973.017 ºC at 760 mmHg |
|
Flash Point |
542.261 ºC |
|
Vapor Pressure |
0mmHg at 25°C |
|
Refractive Index |
1.5280 (estimate) |
|
HS CODE |
29349990 |
|
PSA |
195.43000 |
|
LogP |
6.11850 |
|
Pka |
10.40±0.70(Predicted) |
Synonyms for Rapamycin 53123-88-9: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];
The chemical formula of Rapamycin is C51H79NO13 which containing 51 Carbon atoms,79 Hydrogen atoms,1 Nitrogen atoms and 13 Oxygen atoms,and the molecular weight of Rapamycin is 914.187.
Rapamycin is a member of the macrolide immunosuppressant family and a FRAP inhibitor. Rapamycin exhibits binding and inhibitory actions to the FK506 binding protein (FKBP5) proline rotamase via simultaneous binding by FKBP12 and FRAP. FRAP (RAFT1) proteins exhibit homology to PI 4- and PI 3-kinases, which have PI 4-kinase and autophosphorylating activities. The rapamycin/FKBP complex does not inhibit the FRAP PI 4-kinase activity, but does inhibit FRAP autophosphorylation. Rapamycin is unique in its ability to inhibit lymphokine induced cell proliferation at the G1 and S phase as well as an irreversible cellular arrest at the G1 phase in S. cerevisiae cells. Rapamycin also exhibits selective signal blocking leading to the activation of p70/85 S6 kinase, which is potentially due to the inhibition of FRAP autophosphorylation or protein kinase activity. Rapamycin also exhibits Angiogenesis inhibition, possibly through the inhibition of the Akt pathway. Rapamycin is an inhibitor of mTOR. Rapamycin is also known as Rapamune, 23,27-Epoxy-3H-pyrido[2,1-c] oxaazacyclohentriacontine, AY 22989, and mTOR Inhibitor I.
InChI:InChI=1/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
Relevant articles related to Rapamycin:
|
Article |
Source |
|
Synthesis process for temsirolimus |
- Paragraph 0009; 0010, (2016/12/26) |
|
METHOD FOR PREPARING 42-(DIMETHYLPHOSPHINATE) RAPAMYCIN |
- Paragraph 0047, (2014/03/24) |
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