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61379-65-5

Basic Information
CAS No.: 61379-65-5
Name: Rifapentine
Molecular Structure:
Molecular Structure of 61379-65-5 (Rifapentine)
Formula: C47H64N4O12
Molecular Weight: 877.045
Synonyms: Antibiotic DL 473IT;Cyclopentylrifampicin;DL 473;KTC 1;MDL 473;Prifitin;Priftin;R 77-3;Rifamycin AF/ACPP;
EINECS: 262-743-9
Density: 1.337 g/cm3
Melting Point: 179-180 °C
Boiling Point: 969.3±65.0 °C(Predicted)
Appearance: Crystalline solid
Hazard Symbols: Xi
Risk Codes: 36/37/38
Safety: 26
PSA: 216.66000
LogP: 5.33450
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  • Rifamycin,3-[[(4-cyclopentyl-1-piperazinyl)imino]methyl]-

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History

Rifapentine was first synthesized in 1965 by the same company that produced rifampin. The drug was approved by the Food and Drug Administration (FDA) in June 1998.

Specification

The Rifapentine, with the CAS registry number 61379-65-5, is also known as 3{[(4-Cyclopentyl-1-piperazinyl)imino]methyl}rifamycin. It belongs to the product categories of Active Pharmaceutical Ingredients; Rifapentine; Intermediates & Fine Chemicals; Pharmaceuticals; Chiral Reagents. Its EINECS registry number is 262-743-9. This chemical's molecular formula is C47H64N4O12 and molecular weight is 877.03. What's more, its systematic name is called (7S,11S,12S,13S,14R,15S,16R,17R,18R,26E)-26-{[(4-Cyclopentyl-1-piperazinyl)amino]methylene}-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27-trioxo-8,30-dioxa-24-azatetracyclo [23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl acetate. Rifapentine is an antibiotic drug used in the treatment of tuberculosis.

Physical properties about Rifapentine are: (1)# of Rule of 5 Violations: 3; (2)ACD/BCF (pH 5.5): 3.67; (3)ACD/BCF (pH 7.4): 4.21; (4)ACD/KOC (pH 5.5): 16.58; (5)ACD/KOC (pH 7.4): 19.06; (6)#H bond acceptors: 16; (7)#H bond donors: 6; (8)#Freely Rotating Bonds: 10; (9)Polar Surface Area: 216.66 Å2; (10)Index of Refraction: 1.63; (11)Molar Refractivity: 233.45 cm3; (12)Molar Volume: 655.736 cm3; (13)Polarizability: 92.547×10-24cm3; (14)Surface Tension: 66.20 dyne/cm; (15)Density: 1.337 g/cm3.

Preparation of Rifapentine: this chemical can be prepared by 3-aldehyde rifamycin SV with 1-Amino-4-cyclopentylpiperazine. This reaction needs reagent tetrahydrofuran. The yield is 55 %.

Rifapentine can be prepared by 3-aldehyde rifamycin SV with 1-Amino-4-cyclopentylpiperazine.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C3\C(=C\NN2CCN(C1CCCC1)CC2)\C6=C(\O)c5c3c4C(=O)[C@](Oc4c(c5O)C)(OC=C[C@H](OC)[C@@H]([C@@H](OC(=O)C)[C@@H]([C@@H](O)[C@H](C)[C@H](O)[C@@H](C=CC=C(C(=O)N6)C)C)C)C)C
(2) InChI: InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,48,53-55,57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12?,22-17?,25-14?,32-23+/t24-,26+,27-,28-,33+,38-,39+,43-,47+/m1/s1
(3) InChIKey: RISDZDVHYCURHD-JOXWUWGDSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 710mg/kg (710mg/kg)   Journal of Antibiotics. Vol. 34, Pg. 1026, 1981.
mouse LD50 oral 3300mg/kg (3300mg/kg)   Journal of Antibiotics. Vol. 34, Pg. 1026, 1981.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 242, 1992.
rat LD50 oral > 4gm/kg (4000mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 242, 1992.