Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00592)
Name
Rifapentine
Synonyms    Click to Show/Hide the Synonyms of This API
Priftin; Cyclopentylrifampicin; 61379-65-5; Rifapentin; MDL 473; Priftin (TN); Rifamycin AF/ACPP; CHEBI:45304; MDL-473; 3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin; DL 473; UNII-XJM390A33U; XJM390A33U; Cyclopentyl rifampin; DL-473; R 77-3; C47H64N4O12; (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-8-{(E)-[(4-cyclopentylpiperazin-1-yl)imino]methyl}-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate; DL 473;Cyclopentylrifampicin; Rifapentina; Rifapentinum; NCGC00167431-01; Rifapentinum [Latin]; Rifapentina [Spanish]; Antibiotic DL 473IT; Rifapentine (USAN/INN); 3-(4-Cyclopentyl-1-piperazinyl)iminomethylrifamycin SV; 3-(N-(4-Cyclopentyl-1-piperazinyl)formimidoyl)rifamycin; 3-[N-(4-Cyclopentyl-1-piperazinyl)formimidoyl]rifamycin; CHEMBL1660; DSSTox_CID_21115; DSSTox_RID_79627; DSSTox_GSID_41115; SCHEMBL41590; ANTIBIOTIC DL-473IT; Rifapentine [USAN:INN:BAN]; MDL473; DTXSID8041115; HMS3713M16; DRG-0283; EINECS 262-743-9; Tox21_112435; BDBM50248298; MFCD00866806; AKOS024255723; CCG-220467; DB01201; KS-1409; CAS-61379-65-5; C08059; D00879; J90035; R-77-3; AB01209744-01; AB01209744-03; AB01209744_04; 379R655; M000473; Rifapentine, Antibiotic for Culture Media Use Only; W-105162; (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-{(E)-[(4-cyclopentylpiperazin-1-yl)imino]methyl}-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1(4,7).0(5,28)]triaconta-1(28),1(29),2,4,9,19,21,25,27-nonaen-13-yl acetate; [[(E)-(4-cyclopentylpiperazin-1-yl)iminomethyl]-pentahydroxy-methoxy-heptamethyl-dioxo-[?]yl] acetate; 1279038-35-5
Clinical Status
Approved
Disease Indication Pulmonary tuberculosis ICD-11: 1B10 [1]
PubChem CID
135403821
Formula
C47H64N4O12
Canonical SMILES
C[C@H]1/C=C/C=C(\\C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C=N/N5CCN(CC5)C6CCCC6)/C
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/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1
InChIKey
WDZCUPBHRAEYDL-GZAUEHORSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=135403821"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 877 Topological Polar Surface Area 220
XlogP 6.7 Complexity 1730
Heavy Atom Count 63 Rotatable Bond Count 6
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 15
Full List of Drug Formulations (DFMs) Containing This API
          Rifapentine 150 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Calcium stearate; Fd&c blue no. 2; Sodium ascorbate; Edetate disodium; Ferric oxide red; Propylene glycol; Titanium dioxide; Aluminum oxide; Hydroxypropyl cellulose (1200000 mw); Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified; Sodium starch glycolate type a corn; Starch, corn
                   Dosage Form Oral Tablet
                   Company Sanofi-Aventis
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Calcium stearate; Fd&c blue no. 2; Sodium ascorbate; Ferric oxide red; Propylene glycol; Titanium dioxide; Aluminum oxide; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Sanofi-Aventis
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
References
1 FDA label for approved rifapentine from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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