29-Demethoxyrapamycin

29-Demethoxyrapamycin

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Category Others
Catalog number BBF-00811
CAS 85537-35-5
Molecular Weight 884.14
Molecular Formula C50H77NO12

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Description

29-Demethoxyrapamycin is a triene macrolide produced by Streptomyces hygroscopicus (NRRL 5491). It has anti-S. albicans activity.

Specification

Synonyms AY-24,668
IUPAC Name (12S,15R,16E,23S,24E,26E,28E,30S,32S)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-30-methoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
Canonical SMILES CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)CC(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)C)C)C)OC
InChI InChI=1S/C50H77NO12/c1-30-15-11-10-12-16-31(2)44(60-8)27-38-20-18-36(7)50(59,63-38)47(56)48(57)51-22-14-13-17-39(51)49(58)62-45(35(6)25-37-19-21-40(52)46(26-37)61-9)29-43(55)34(5)24-33(4)42(54)28-41(53)32(3)23-30/h10-12,15-16,24,30,32,34-40,42,44-46,52,54,59H,13-14,17-23,25-29H2,1-9H3/b12-10+,15-11+,31-16+,33-24+/t30-,32?,34-,35-,36?,37+,38+,39?,40?,42?,44+,45+,46-,50?/m1/s1
InChI Key SRIDGLJAFSFWOP-BUKAIXPZSA-N

Properties

Appearance White Crystal
Antibiotic Activity Spectrum yeast
Melting Point 122-124°C

Reference Reading

1. Activity of rapamycin (AY-22,989) against transplanted tumors
C P Eng, S N Sehgal, C Vézina J Antibiot (Tokyo). 1984 Oct;37(10):1231-7. doi: 10.7164/antibiotics.37.1231.
Rapamycin exhibits activity against several ascites and solid transplantable tumors; it is slightly active to inactive against leukemias. On a weight basis, rapamycin was less active than 5-fluorouracil, cyclophosphamide and adriamycin, but rapamycin's maximal activity against Colon 38 tumor was similar to that of 5-fluorouracil and cyclophosphamide. Its activity was such that it significantly inhibited tumor growth at any stage of development. In the active dose range, rapamycin appeared less toxic than the other drugs. In the Colon 38 tumor model, rapamycin at a given dose exhibited the same activity when administered ip, iv, im and sc; upon oral administration, its activity was reduced but not abolished. Rapamycin was compatible with 5-fluorouracil and cyclophosphamide. The sequential treatment 5-fluorouracil-rapamycin-cyclophosphamide was superior to the sequence 5-fluorouracil-adriamycin-cyclophosphamide in protecting Colon 38 tumor-bearing mice. 29-Demethoxyrapamycin exerted only marginal activity against P388 lymphocytic leukemia; it was inactive against B16 melanocarcinoma and Colon 38 solid tumor.

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