Rifamycin,3-[[(4-cyclopentyl-1-piperazinyl)imino]methyl]-

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.

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 %.

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.