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Tenofovir disoproxil fumarate(CAS No. 202138-50-9)

Tenofovir disoproxil fumarate C19H30N5O10P.C4H4O4 (cas 202138-50-9) Molecular Structure

202138-50-9 Structure

Identification and Related Records

【Name】
Tenofovir disoproxil fumarate
【Iupac name】
[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-
yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate;
(E)-but-2-enedioic acid
【CAS Registry number】
202138-50-9
【Synonyms】
TDF
PMPA prodrug
Tenofovir Disoproxil Fumarate [USAN]
9-((R)-2-((Bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine, fumarate
201341-05-1
Bis(NeopentylOC)PMPA
Viread
GS 4331-05 (*1:1 Fumarate salt*)
Viread (*1:1 Fumarate salt*)
Truvada
Tenofovir DF
[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate
【Molecular Formula】
C19H30N5O10P.C4H4O4 (Products with the same molecular formula)
【Molecular Weight】
635.514921
【Inchi】
InChI=1S/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1
【InChIKey】
VCMJCVGFSROFHV-WZGZYPNHSA-N
【Canonical SMILES】
CC(C)OC(=O)OCOP(=O)(COC(C)CN1C=NC2=C1N=CN=C2N)OCOC(=O)OC(C)C.C(=CC(=O)O)C(=O)O
【Isomers smiles】
C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C.C(=C/C
(=O)O)\C(=O)O
【MOL File】
202138-50-9.mol

Chemical and Physical Properties

【Appearance】
white to pink crystalline
【Density】
1.45 g/cm3
【Melting Point】
219 C
【Boiling Point】
642.7 °C at 760 mmHg
【Vapour】
2.06E-16mmHg at 25°C
【Flash Point】
342.5 °C
【Water】
13.4 mg/ml
【Solubilities】
13.4 mg/ml Appearance:white to pink crystalline
Transport Information: OTH
Hazard Symbols:UN NO.
particular:particular
【Computed Properties】
Molecular Weight:635.514921 [g/mol]
Molecular Formula:C23H34N5O14P
H-Bond Donor:3
H-Bond Acceptor:14
Rotatable Bond Count:19
Tautomer Count:3
Exact Mass:635.183987
MonoIsotopic Mass:635.183987
Topological Polar Surface Area:260
Heavy Atom Count:43
Formal Charge:0
Complexity:817
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Hazard Codes】
Xi
【Risk Statements】
R36/37/38
【Safety Statements 】
26-36
【Transport】
OTH
【Formulations/Preparations】
Oral: Tablets, film-coated, 300 mg, Viread, Gilead
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl tenofovir disoproxil fumarate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

The Tenofovir disoproxil fumarate with the cas number 202138-50-9, is also called (1)(R)-5-((2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)-2,4,6,8-tetraoxa-5-phosphanonanedioic acid, bis(1-methylethyl) ester, 5-oxide, (E)-2-butenedioate (1:1); (2)9-((R)-2-((Bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine fumarate (1:1) ; (3)Bis(hydroxymethyl) (((R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)phosphonate, bis(isopropyl carbonate)(ester), fumarate (1:1); (4) PMPA prodrug ; (5) TDF ; (6) Tenofovir DF ; (7) Tenofovir disoproxil fumarate ; (8) UNII-OTT9J7900I ; (9) Viread.

Properties of Tenofovir disoproxil fumarate are: (1)ACD/LogP: 2.04 ; (2)# of Rule of 5 Violations: 2 ; (3)ACD/LogD (pH 5.5): 2.01 ; (4)ACD/LogD (pH 7.4): 2.04 ; (5)ACD/BCF (pH 5.5): 19.53 ; (6)ACD/BCF (pH 7.4): 20.78 ; (7)ACD/KOC (pH 5.5): 286.95 ; (8)ACD/KOC (pH 7.4): 305.32 ; (9)#H bond acceptors: 15 ; (10)#H bond donors: 2 ; (11)#Freely Rotating Bonds: 17 ; (12)Polar Surface Area: 172.47 ?2 ; (13)Flash Point: 342.5 °C ; (14)Enthalpy of Vaporization: 94.85 kJ/mol ; (15)Boiling Point: 642.7 °C at 760 mmHg ; (16)Vapour Pressure: 2.06E-16 mmHg at 25°C

The Tenofovir disoproxil fumarate has a brand name VIREAD. It is obtained from a fumaric acid salt of bis-isopropoxycarbonyloxymethyl ester derivative of tenofovir. Tenofovir disoproxil fumarate is converted to tenofovir, which is an acyclic nucleoside phosphonate (nucleotide) analog of adenosine 5'-monophosphate. Tenofovir exhibits activity against HIV-1 reverse transcriptase. VIREAD are taken orally . The most common aderse reactions include: light to moderate gastrointestinal upset (diarrhea, nausea, vomiting, and flatulence), Metabolic system of low incidence (1%) disease phosphatase, serum phosphate light to moderate decrease. It can also show dangerous lactic acidosis.

You can still convert the following datas into molecular structure :
1. O=C(O)\C=C\C(=O)O.O=P(OCOC(=O)OC(C)C)(OCOC(=O)OC(C)C)CO[C@H](C)Cn1c2ncnc(c2nc1)N
2. InChI=1/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS.
- Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template.
【Therapeutic Uses】
Tenofovir is indicated, in combination with other antiretroviral agents, for treatment of HIV-1 infection. /Included in US product labeling/
Chronic viral hepatitis has emerged as one of the leading causes of morbidity and mortality among HIV-positive patients. These individuals are at risk for aggressive chronic active hepatitis, cirrhosis, and hepatocellular carcinoma, and eventually, death. Currently available therapies for hepatitis B are limited and include interferon-alpha, lamivudine (3TC), and adefovir. Tenofovir (TDF), a recently approved drug for the treatment of HIV, is also active against hepatitis B. the case of a HIV-positive patient with liver cirrhosis secondary to chronic hepatitis B virus (HBV) with evidence of resistance to 3TC /was reported/. The patient was initially accepted as a liver transplant candidate. However, when TDF was added to his treatment, a remarkable virologic and histopathologic improvement was achieved. The patient was subsequently removed from the liver transplant program and has not suffered from any further hepatic complications. [Ristig M et al; AIDS Patient Care STDS 17 (9): 439-42 (2003)]
【Biomedical Effects and Toxicity】
Tenofovir is eliminated by a combination of glomerular filtration and active tubular secretion. There may be competition for elimination with other compounds that are also renally eliminated.
Following intravenous administration, approximately 70-80% of tenofovir is eliminated unchanged in the urine within 72 hours; following multiple oral doses of tenofovir 300 mg once a day (under fed conditions), 32 +/- 10% of the administered dose is recovered in urine over 24 hours.
Volume of distribution at steady state: 1.3 +/- 0.6 l/kg and 1.2 +/- 0.4 l/kg, following intravenous administration of tenofovir at doses of 1 and 3 mg/kg body weight, respectively.
Oral bioavailability of tenofovir in fasted patients is approximately 25%. Following a single oral dose of 300 mg, the area under the plasma concentration-time curve (AUC) is 2287 +/- 685 ng*hours per ml. NOTE: Administration of food (high in fat meal containing 40-50% fat) increases the oral bioavailability, with an increase in the AUC of approximately 40%.
Plasma tenofovir concentrations and area under the plasma concentration-time curve (AUC) are increased when the drug is administered with a high-fat meal, and administration with a meal is recommended to enhance bioavailability of the drug.
It is unknown whether tenofovir is distributed into human breast milk. However, it is distributed into the milk in lactating rats.

Supplier Location

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