Oseltamivir phosphate

Iupac Name：ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate;phosphoric acid

CAS No.: 204255-11-8

Molecular Weight：410.404

Modify Date.: 2022-11-25 01:19

Introduction: Oseltamivir was launched in the US and Switzerland for the treatmentof influenza infections by all common strain viruses. It can be obtained by atleast 2 different ways including a novel 12-step synthesis from (-)-quinic acid.Oseltamivir is the ethyl ester prodrug of GS-4071, the corresponding acid, whichis one of the most potent inhibitors of both influenza A and B virusneuraminidase (sialidase) isoenzymes; these glycoproteins are expressed onthe virion surface and are essential for virus replication for both A and B strains.Oseltamivir emerged as one of the first two neuraminidase inhibitors to reachthe market. GS-4071 demonstrated a low (< 5%) oral bioavailability inanimals due to a poor absorption from the gastrointestinal barrier; byincorporating a more lipophilic ester group, the oral bioavailabilty can reach 30to 100% in mice, rats and dogs. Following oral administration of Oseltamivir inrats, a similar concentration of GS-4071 was found in the bronchoalveolar liningfluid and the plasma which indicated a good penetration of the active compoundinto the lower respiratory tract. In mice, chickens and ferrets, orallyadministered Oseltamivir was found to have significant inhibitory effects on Aand B influenza infections in protecting against a lethal challenge of virus andlessening virus titer in the lungs or nasal washings. In several clinical trials withpatients receiving oral capsules daily, Oseltamivir was shown to be effective inreducing significantly the duration and severity of the clinical symptoms,including fever, cough and general malaise, in both early treatment andprevention. View more+

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1. Names and Identifiers

1.1 Name: Oseltamivir phosphate
1.2 Synonyms: (3R,4R,5S)-ethyl 4-acetaMido-5-aMino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate phosphate (3R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate phosphate 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)-, phosphate (1:1) acide phosphorique - (3R,4R,5S)-4-(acétylamino)-5-amino-3-(1-éthylpropoxy)cyclohex-1-ène-1-carboxylate d'éthyle (1:1) ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate phosphate ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate phosphate (1:1) Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(3-pentanyloxy)-1-cyclohexene-1-carboxylate phosphate (1:1) Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate phosphate (1:1) GS-4104/002 MFCD08059548 NTERMEDIATES OF OSELTAMIVIR Oselt Oseltamir phosphate Oseltamivir (phosphate) OseltaMivir Acid-D3 Phosphate Oseltamivir phosphat Oseltamivir Phosphate (200 mg) OseltaMivir phosphate (TaMiflu) Osteltamivir phosphate Phosphorosäure-ethyl-(3R,4R,5S)-4-(acetylamino)-5-amino-3-(1-ethylpropoxy)cyclohex-1-en-1-carboxylat(1:1) Ro 64-0796/002 Ro-64-0796/002 Tamiflu

1.3 CAS No.: 204255-11-8

1.4 CID: 78000

1.5 EINECS(EC#): 616-396-9

1.6 Molecular Formula: C16H31N2O8P (isomer)

1.7 Inchi: InChI=1S/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19;1-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19);(H3,1,2,3,4)/t13-,14+,15+;/m0./s1

1.8 InChkey: PGZUMBJQJWIWGJ-ONAKXNSWSA-N

1.9 Canonical Smiles: CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O

1.10 Isomers Smiles: CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O

2. Properties

2.1 Density: 1.08

2.1 Melting point: 197-212°C

2.1 Boiling point: 473.3 °C at 760 mmHg

2.1 Flash Point: 240 °C

2.1 Precise Quality: 410.18200

2.1 PSA: 178.22000

2.1 logP: 1.44800

2.1 Solubility: H2O: soluble30mg/mL, clear

2.2 Appearance: white to beige

2.3 Storage: -20°C Freezer

2.4 Chemical Properties: White Cyrstalline Solid

2.5 Color/Form: white to beige

2.6 pKa: pKa = 7.7 at 25 deg C (primary amine)

2.7 Water Solubility: H2O: soluble 30mg/mL, clear

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 General Description: receptor site showed clearly that additional binding sitesexist for the C-5 acetamido carbonyl group and the arginineresidue at position 152 of the receptor site. In addition, the C-2 carboxyl group of sialic acid binds to Arg 118, Arg 292, andArg 371. Position C-6 is capable of undergoing a hydrophobicinteraction with various amino acids, including Glu, Ala,Arg, and Ile. Maximum binding to neuraminidase occurswhen the C-6 substituent is substituted with a nonpolar chain.In oseltamivir, this nonpolar group is 3-pentyl. An importantfeature of oseltamivir is the ethyl ester, which makes the drugorally efficacious. This drug is the first orally active agent foruse against influenza A and B. It is also indicated for the treatmentof acute illness. If administered within 2 days after theonset of influenza symptoms, the drug is effective.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 4 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302+H312+H332 (50%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H317 (50%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P333+P313, P337+P313, P363, and P501

3.3 Methods of Manufacturing: N. W. Bischofberger et al., US Patent 5763483 (1998 to Gilead Sci.).

3.4 Usage: Oseltamivir Phosphate is an orally active inhibitor of influenza virus neuraminidase; converted in vivo to the active acid metabolite. An antiviral drug. It is a COVID19-related research product.

4. Safety and Handling

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl oseltamivir phosphate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Oseltamivir phosphate/

4.2 Octanol/Water Partition Coefficient: log Kow = 0.95 (est)

4.3 Hazard Class: IRRITANT

4.3 Hazard Declaration: H302+H312+H332

4.3 DisposalMethods: 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.

4.4 RIDADR: NONH for all modes of transport

4.4 Caution Statement: P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P333+P313, P337+P313, P363, P501

4.4 Formulations/Preparations: Oral: Capsules: 75 mg (of oseltamivir) (Tamiflu), (Roche); For Suspension: 12 mg (of oseltamivir) per mL (Tamiflu), (Roche). /Oseltamivir phosphate/

4.5 Report

The Oseltamivir phosphate, with its CAS registry number 204255-11-8, has the IUPAC name of ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate; phosphoric acid. For being a kind of white cyrstalline solid, it is usually applied as an antiviral drug, with its product categories including API; Intermediates & Fine Chemicals; Pharmaceuticals; Ring Systems; Oseltamivir; Influenza Viruses.

The characteristics of this chemical are as below: (1)ACD/LogP: 1.50; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.02; (4)ACD/LogD (pH 7.4): 0.69; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.25; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 24.06; (9)#H bond acceptors: 6; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 59.08; (13)Flash Point: 240 °C; (14)Enthalpy of Vaporization: 73.64 kJ/mol; (15)Boiling Point: 473.3 °C at 760 mmHg; (16)Vapour Pressure: 3.98E-09 mmHg at 25°C; (17)Exact Mass: 410.181802; (18)MonoIsotopic Mass: 410.181802; (19)Topological Polar Surface Area: 168; (20)Heavy Atom Count: 27; (21)Complexity: 468.

What's more, the following datas could be converted into the molecular structure:
(1)Canonical SMILES: CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O
(2)Isomeric SMILES: CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O
(3)InChI: InChI=1S/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19;1-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19);(H3,1,2,3,4)/t13-,14+,15+;/m0./s1
(4)InChIKey: PGZUMBJQJWIWGJ-ONAKXNSWSA-N?

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4.6 Specification

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1

Eye irritation, Category 2

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H317 May cause an allergic skin reaction H319 Causes serious eye irritation H412 Harmful to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P273 Avoid release to the environment.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

204255-11-8Total: 88 Synthesis Route

77-76-9 173 Suppliers

204255-11-8 219 Suppliers

Literatures:
US2014/51756 A1, ;
Yield: null

77-95-2 78 Suppliers

204255-11-8 219 Suppliers

Literatures:
US2014/51756 A1, ;
Yield: null

96-22-0 104 Suppliers

204255-11-8 219 Suppliers

Literatures:
Tetrahedron Letters, , vol. 53, # 13 p. 1561 - 1563
Yield: null

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7. Precursor and Product

precursor:

196618-13-0

757965-01-8

204255-06-1

138-59-0

930275-48-2

930275-47-1

367252-67-3

367252-68-4

927395-71-9

367252-65-1

367252-66-2

204254-81-9

943515-58-0

127604-94-8

5709-98-8

32384-42-2

332047-23-1

101769-63-5

77-95-2

96-22-0

651324-04-8

651324-06-0

3458-28-4

77-76-9

651324-07-1

View all

8. Other Information

8.0 Target: Value

8.1 Uses: Oseltamivir Phosphate is an orally active inhibitor of influenza virus neuraminidase; converted in vivo to the active acid metabolite. An antiviral drug. It is a COVID19-related research product.

8.2 Anti-influenza virus: Oseltamivir phosphate is a kind of anti-influenza drugs, under the trade name Tamiflu. Its appearance exhibits as white to yellowish-white powder. It can be divided into type A (alpha) and B (Beta) selective inhibitor of the influenza virus neuraminidase and can prevent the release of virus from infected cells, through inhibiting the activity of the influenza virus neuraminidase, thus achieving the purpose of control of influenza symptoms. Clinically it can be used for treatment of the type A influenza and type B influenza in adults and children of 1 year old or over 1 year old as well as the clinical prevention of influenza A and B in adult and adolescent of 13 year old or over 13 years old.
Oseltamivir phosphate can subject to rapid metabolism into oselatamivr carboxylate after gastrointestinal absorption with 75% of the total oral administrated dose participating in the systemic circulation in the from of oselatamivr carboxylate. The active ingredient of this drug is a potent and unique neuraminidase inhibitors acting on all the processes of influenza virus infection, preventing the replication of all clinically relevant influenza virus strains A or B strain. It has obvious inhibitory effect even in nanomolar concentration in vitro. It has ben observed in vitro that the active metabolite can inhibit the growth of influenza virus as well as in vivo that it can inhibit the replication and pathogenicity of influenza virus. This product, through inhibiting the release of virus from infected cells, can reduce the spread of influenza A or B virus.

8.3 Uses: Antibiotics and anti-virus

8.4 Description: Oseltamivir was launched in the US and Switzerland for the treatment of influenza infections by all common strain viruses. It can be obtained by at least 2 different ways including a novel 12-step synthesis from (-)-quinic acid. Oseltamivir is the ethyl ester prodrug of GS-4071, the corresponding acid, which is one of the most potent inhibitors of both influenza A and B virus neuraminidase (sialidase) isoenzymes; these glycoproteins are expressed on the virion surface and are essential for virus replication for both A and B strains. Oseltamivir emerged as one of the first two neuraminidase inhibitors to reach the market. GS-4071 demonstrated a low (< 5%) oral bioavailability in animals due to a poor absorption from the gastrointestinal barrier; by incorporating a more lipophilic ester group, the oral bioavailabilty can reach 30 to 100% in mice, rats and dogs. Following oral administration of Oseltamivir in rats, a similar concentration of GS-4071 was found in the bronchoalveolar lining fluid and the plasma which indicated a good penetration of the active compound into the lower respiratory tract. In mice, chickens and ferrets, orally administered Oseltamivir was found to have significant inhibitory effects on A and B influenza infections in protecting against a lethal challenge of virus and lessening virus titer in the lungs or nasal washings. In several clinical trials with patients receiving oral capsules daily, Oseltamivir was shown to be effective in reducing significantly the duration and severity of the clinical symptoms, including fever, cough and general malaise, in both early treatment and prevention.

8.5 Chemical Properties: White Cyrstalline Solid

8.6 Originator: Gilead (US)

8.7 Uses: Orally active inhibitor of influenza virus neuraminidase; converted in vivo to the active acid metabolite. An antiviral drug.

8.8 Uses: Oseltamivir phosphate (Tamiflu) is a competitive neuraminidase inhibitor. The prodrug oseltamivir phosphate (Tamiflu) is itself not virally effective; however, once in the liver, it is converted by natural chemical processes, hydrolysed hepatically to its

8.9 Uses: An antiviral agent

8.10 Manufacturing Process: To a suspension of shikimic acid (25 g, 144 mmol, Aldrich) in methanol (300 ml) was added p-toluenesulfonic acid (274 mg, 1.44 mmol, 1 mol %) and the mixture was heated to reflux for 2 h. After adding more p-toluenesulfonic acid (1 mol %) the reaction was refluxed for 26 h and was evaporated. The crude methyl ester (28.17 g) was suspended in acetone (300 ml) and was treated with dimethoxypropane (35 ml, 288 mmol) and was stirred at room temperature for 6 h and then was evaporated. The crude product was dissolved in ethyl acetate (400 ml) and was washed with saturated NaHCO3 (3 times 125 ml) and saturated NaCl. The organic phase was dried (MgSO4), filtered, and evaporated to afford crude 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-carboxylic acid methyl ester (about 2.94 g).
To a solution of 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-carboxylic acid methyl ester (29.4 g, 141 mmol) in CH2Cl2, (250 ml) at 0°C was added triethylamine (29.5 ml, 212 mmol) followed by the addition of methanesulfonyl chloride (13.6 ml, 176 mmol) over a period of 10 min. The reaction was stirred at 0°C for 1 h and ice cold water (250 ml) was added. After transfer to a separatory funnel, the organic phase was washed with water, 5% citric acid (300 ml), saturated NaHCO3 (300 ml) and was dried (MgSO4), filtered, and evaporated. The crude product was filtered through a short plug of silica gel on a fritted glass funnel eluting with ethyl acetate. The filtrate was evaporated to afford 7-methanesulfonyloxy-2,2-dimethyl- 3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-carboxylic acid methyl ester (39.5 g, 91%) as a viscous oil.
To a solution of 7-methanesulfonyloxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-carboxylic acid methyl ester (35.85 g, 117 mmol) in methanol (500 ml) was added p-toluenesulfonic acid (1.11 g, 5.85 mmol, 5 mol %) and the solution was refluxed for 1.5 h and was evaporated. The residue was redissolved in methanol (500 ml) and was refluxed an additional 4 h. The solvent was evaporated and the crude oil was triturated with diethyl ether (250 ml). After completing the crystallization overnight at 0°C, the solid was filtered and was washed with cold diethyl ether, and dried to afford 3,4- dihydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester (24.76 g) as a white solid. Evaporation of the filtrate and crystallization of the residue from methanol/diethyl ether gave an additional 1.55 g. Obtained 26.3 g (85%) of the 3,4-dihydroxy-5-methanesulfonyloxy-cyclohex-1-ene-1- carboxylic acid methyl ester.
A suspension of 3,4-dihydroxy-5-methanesulfonyloxy-cyclohex-1-ene-1- carboxylic acid methyl ester (20.78 g, 78 mmol) in tetrahydrofuran (400 ml) at 0°C was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (11.7 ml, 78 mmol) and was stirred at room temperature for 9 h at which time the reaction was complete. The reaction was evaporated and the crude residue was dissolved in CH2Cl2 (200 ml) and was washed with saturated NaCl (300 ml). The aqueous phase was extracted with CH2Cl2 (2 times 200 ml). The combined organic extracts were dried (MgSO4), filtered, and evaporated. The crude product was purified on silica gel (ethyl acetate) to afford 5-hydroxy-7- oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester (12 g, 90%) as a white solid.

8.11 Brand name: Tamiflu (Roche).

8.12 Therapeutic Function: Antiviral

8.13 General Description: receptor site showed clearly that additional binding sitesexist for the C-5 acetamido carbonyl group and the arginineresidue at position 152 of the receptor site. In addition, the C-2 carboxyl group of sialic acid binds to Arg 118, Arg 292, andArg 371. Position C-6 is capable of undergoing a hydrophobicinteraction with various amino acids, including Glu, Ala,Arg, and Ile. Maximum binding to neuraminidase occurswhen the C-6 substituent is substituted with a nonpolar chain.In oseltamivir, this nonpolar group is 3-pentyl. An importantfeature of oseltamivir is the ethyl ester, which makes the drugorally efficacious. This drug is the first orally active agent foruse against influenza A and B. It is also indicated for the treatmentof acute illness. If administered within 2 days after theonset of influenza symptoms, the drug is effective.

8.14 Mesh: Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

8.15 Mesh Entry Terms: GS 4071

8.16 Use Classification: Human drugs -> Tamiflu -> EMA Drug Category|Antivirals for systemic use -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

8.17 Biochem/physiol Actions: Oseltamivir phosphate is an influenza viral neuraminidase inhititor. Oseltamivir phosphate, an antiviral, is used clinically to treat influenza A and influenza B, and to prevent flu after exposure. Oseltamivir phosphate is hydrolyzed in the liver to its active form, oseltamivir carboxylate, which is an inhibitor of influenza viral neuraminidases essential for viral replication. Oseltamivir has a broad spectrum of activity against a range of influenza A and B subtypes with IC50 values for neuraminidases measured from less than 1 nM to approximately 30 nM, depending on the virus subtype.

8.18 Clinical Use: Oseltamivir was approved as the first orally administered neuraminidase inhibitor used against influenza A and B viruses. The drug is indicated for the treatment of uncomplicated acute illness caused by influenza infection.

8.19 Side effects: Side effects with oseltamivir are minor, consist of nausea and vomiting, and occur primarily in the first two days of therapy.

8.20 Veterinary Drugs and Treatments: Although, there is no research published (at the time of writing— January 2007) documenting oseltamivir safety or efficacy in dogs or cats, there is much interest and discussion regarding its potential for the adjunctive treatment of parvovirus infections in dogs. It may be of benefit for adjunctive treatment of other viral infections, particularly those with associated secondary bacterial components, but research or experience is lacking. A recent study performed in horses, experimentally infected with equine influenza A (H3N8), documented some efficacy in the attenuation of clinical signs (pyrexia), viral shedding, and secondary bacterial pneumonias (Yamanaka, Tsujimura et al. 2006).
Because oseltamivir is the primary antiviral agent proposed for treatment or prophylaxis for an H5N1 influenza (“bird flu”) pandemic in humans, its use in veterinary patients is controversial, particularly due to concerns of adequate drug supply for the human population and the potential for influenza virus resistance development. In 2006, the FDA banned the extra-label use of oseltamivir and other influenza antivirals in chickens, turkeys and ducks. At the time of writing, its use is still allowed in mammal veterinary patients, but veterinarians should use the drug prudently and be cognizant of these public health concerns.

8.21 Metabolism: Oseltamivir is readily absorbed from the GI tract following oral administration. It is a prodrug that is extensively metabolized in the liver, undergoing ester hydrolysis to the active carboxylic acid. Two oxidative metabolites also have been isolated, with the major oxidation product being the ω-carboxylic acid.

9. Computational chemical data

Molecular Weight: 410.404g/mol
Molecular Formula: C₁₆H₃₁N₂O₈P
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 410.18180295
Monoisotopic Mass: 410.18180295
Complexity: 468
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 9
Topological Polar Surface Area: 168
Heavy Atom Count: 27
Defined Atom Stereocenter Count: 3
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB7PAIAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAHgAQCCAADDzhgAYCCALABBCIQiHSGIAAAAAgAAAACIEIAEgCRBIAoQAXEAAGlgCYIYO82SOQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(3-pentanyloxy)-1-cyclohexene-1-carboxylate phosphate (1:1)

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CAS 204255-11-8 Oseltamivir phosphate