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Oseltamivir Impurities

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(3R

(3R,4R,5R)- Oseltamivir hydrochloride

  • CAT Number DCTI-C-000640
  • CAS Number 1402431-91-7 (Free base)
  • Molecular Formula C16H29ClN2O4 (HCl Salt) C16H28N2O4 (Free base)
  • Molecular Weight 348.87 (HCl Salt) 312.41 (Free base)
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(3R,4R,5S)-ethyl -4-acetamido-5-(((Z)-(5-(hydroxy ...

  • CAT Number DCTI-C-000659
  • CAS Number NA
  • Molecular Formula C22H32N2O6
  • Molecular Weight 420.51
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(3R

(3R,4S,5R)- Oseltamivir hydrochloride

  • CAT Number DCTI-C-000641
  • CAS Number 941296-96-4 (Free base)
  • Molecular Formula C16H29ClN2O4 (HCl Salt) C16H28N2O4 (Free base)
  • Molecular Weight 348.87 (HCl Salt) 312.41 (Free base)
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(3R,4S,5S)- Oseltamivir hydrochloride

(3R,4S,5S)- Oseltamivir hydrochloride

  • CAT Number DCTI-C-000658
  • CAS Number 2413185-95-0
  • Molecular Formula C16H29ClN2O4 (HCl Salt) C16H28N2O4 (Free base)
  • Molecular Weight 348.87 (HCl Salt) 312.41 (Free base)
Detailed View

(3S,4R,5R)- Oseltamivir hydrochloride

  • CAT Number DCTI-C-000660
  • CAS Number 2081110-44-1
  • Molecular Formula C16H29ClN2O4 (HCl Salt) C16H28N2O4 (Free base)
  • Molecular Weight 348.87 (HCl Salt) 312.41 (Free base)
Detailed View
(3S

(3S,4R,5S)- Oseltamivir hydrochloride

  • CAT Number DCTI-C-000642
  • CAS Number 2081110-43-0 (Free base)
  • Molecular Formula C16H29ClN2O4 (HCl Salt) C16H28N2O4 (Free base)
  • Molecular Weight 348.87 (HCl Salt) 312.41 (Free base)
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(3S,4S,5R)- Oseltamivir hydrochloride

(3S,4S,5R)- Oseltamivir hydrochloride

  • CAT Number DCTI-C-000643
  • CAS Number 1035895-88-5 (free base)
  • Molecular Formula C16H29ClN2O4 (HCl Salt) C16H28N2O4 (Free base)
  • Molecular Weight 348.87 (HCl Salt) 312.41 (Free base)
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(3S,4S,5S)- Oseltamivir hydrochloride

(3S,4S,5S)- Oseltamivir hydrochloride

  • CAT Number DCTI-C-000644
  • CAS Number NA
  • Molecular Formula C16H29ClN2O4 (HCl Salt) C16H28N2O4 (Free base)
  • Molecular Weight 348.87 (HCl Salt) 312.41 (Free base)
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1,2-Dihydro-Oseltamivir

1,2-Dihydro-Oseltamivir

  • CAT Number DCTI-C-001501
  • CAS Number 1052063-38-3
  • Molecular Formula C16H30N2O4
  • Molecular Weight 314.43
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4-N-Desacetyl-5-N-acetyl Oseltamivir

  • CAT Number DCTI-C-004969
  • CAS Number 956267-10-0
  • Molecular Formula C16H28N2O4
  • Molecular Weight 312.41
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Ethyl (1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4...

  • CAT Number DCTI-C-003073
  • CAS NUMBER 204255-02-7
  • MOLECULAR FORMULA C14H23NO3
  • MOLECULAR WEIGHT 253.34
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Ethyl (1S, 5R, 6S)-5-(pentan-2-yloxy)-7-oxabicyclo [4.1.0] hept-3-ene-3-carboxylate

Ethyl (1S, 5R, 6S)-5-(pentan-2-yloxy)-7-oxabicyclo...

  • CAT Number DCTI-C-001026
  • CAS Number NA
  • Molecular Formula C14H22O4
  • Molecular Weight 254.32
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Ethyl (1S, 5R, 6S)-5-(sec- butoxy)-7-oxabicyclo [4.1.0] hept-3-ene-3-carboxylate

Ethyl (1S, 5R, 6S)-5-(sec- butoxy)-7-oxabicyclo [4...

  • CAT Number DCTI-C-001027
  • CAS Number NA
  • Molecular Formula C13H20O4
  • Molecular Weight 240.3
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Ethyl (3R,4R,5R)-5-chloro-4-hydroxy-3-(pentan-3-yl...

  • CAT Number DCTI-C-002672
  • CAS NUMBER 2762080-42-0
  • MOLECULAR FORMULA C14H23ClO4
  • MOLECULAR WEIGHT 290.78
Detailed View

Ethyl (3R,4R,5S)-4-acetamido-5-(((5-formylfuran-2-...

  • CAT Number DCTI-C-002094
  • CAS NUMBER NA
  • MOLECULAR FORMULA C22H32N2O6
  • MOLECULAR WEIGHT 420.51
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Ethyl 5-(Acetylamino)-3-hydroxybenzoate

  • CAT Number DCTI-C-004376
  • CAS Number NA
  • Molecular Formula C11H13NO4
  • Molecular Weight 223.23
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Oseltamivir -D5

Oseltamivir -D5

  • CAT Number DCTI-A-000171
  • CAS Number 2140263-19-8(HCl)
  • Molecular Formula C16H24D5ClN2O4 (HCl Salt) C16H23D5N2O4 (Free base)
  • Molecular Weight 353.9 (HCl Salt) 317.44(Free base)
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Oseltamivir Carboxylic Acid

Oseltamivir Carboxylic Acid

  • CAT Number DCTI-C-000152
  • CAS Number 187227-45-8 (free acid)
  • Molecular Formula C14H25ClN2O4 (HCl Salt) C14H24N2O4 (Free base)
  • Molecular Weight 320.81 (HCl Salt) 284.36 (Free base)
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Oseltamivir Carboxylic acid - D3 HCl

Oseltamivir Carboxylic acid – D3 HCl

  • CAT Number DCTI-A-000172
  • CAS Number 1242184-43-5
  • Molecular Formula C14H22D3ClN2O4 (HCl Salt) C14H21D3N2O4 (Free base)
  • Molecular Weight 323.83 (HCl Salt) 287.37 (Free base)
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Oseltamivir citric acid Adduct

Oseltamivir citric acid Adduct

  • CAT Number DCTI-C-000808
  • CAS Number 2738248-86-5
  • Molecular Formula C22H34N2O10
  • Molecular Weight 486.52
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Oseltamivir Citric Acid Adduct-2

  • CAT Number DCTI-C-001502
  • CAS Number 2738248-87-6
  • Molecular Formula C22H34N2O10
  • Molecular Weight 486.52
Detailed View
Oseltamivir Diamine

Oseltamivir Diamine

  • CAT Number DCTI-C-001028
  • CAS Number 212504-89-7
  • Molecular Formula C14H26N2O3
  • Molecular Weight 270.37
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Oseltamivir Diamine Acid

  • CAT Number DCTI-C-002703
  • CAS NUMBER NA
  • MOLECULAR FORMULA C12H22N2O3 (Free base); C12H23ClN2O3 (HCl salt)
  • MOLECULAR WEIGHT 242.32 (free base); 278.78 (HCl salt)
Detailed View
Oseltamivir EP Impurity A Hydrochloride

Oseltamivir EP Impurity A Hydrochloride

  • CAT Number DCTI-C-000237
  • CAS Number 1364932-19-3(freebase)
  • Molecular Formula C14H25ClN2O4 (HCl Salt) C14H24N2O4 (Free base)
  • Molecular Weight 320.81 (HCl Salt) 284.36 (Free base)
Detailed View
Oseltamivir EP Impurity E

Oseltamivir EP Impurity E

  • CAT Number DCTI-C-001080
  • CAS Number 208720-71-2 (Free Base)
  • Molecular Formula C15H29N2O8P (Phospate Salt) C15H26N2O4 (Free base)
  • Molecular Weight 396.38 (Phospate Salt) 298.38 (Free base)
Detailed View

Oseltamivir EP Impurity F

  • CAT Number DCTI-C-002819
  • CAS NUMBER 1052063-37-2
  • MOLECULAR FORMULA C15H26N2O4
  • MOLECULAR WEIGHT 298.38
Detailed View
Oseltamivir EP Impurity-D

Oseltamivir EP Impurity-D

  • CAT Number DCTI-C-000845
  • CAS Number 1346604-18-9
  • Molecular Formula C11H13NO4
  • Molecular Weight 223.23
Detailed View
Oseltamivir Glucose Adduct-1

Oseltamivir Glucose Adduct-1

  • CAT Number DCTI-C-001202
  • CAS Number NA
  • Molecular Formula C22H38N2O9
  • Molecular Weight 474.55
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Oseltamivir Hydrochloride-D3

Oseltamivir Hydrochloride-D3

  • CAT Number DCTI-A-000180
  • CAS Number 1093851-61-6(freeamine)
  • Molecular Formula C16H26D3ClN2O4 (HCl Salt) C16H25D3N2O4 (Free base)
  • Molecular Weight 351.89 (HCl Salt) 315.43 (Free base)
Detailed View
Oseltamivir impurity 24

Oseltamivir impurity 24

  • CAT Number DCTI-C-001761
  • CAS NUMBER 2417645-75-9
  • MOLECULAR FORMULA C18H31NO3
  • MOLECULAR WEIGHT 309.45
Detailed View
Oseltamivir impurity 59

Oseltamivir impurity 59

  • CAT Number DCTI-C-001096
  • CAS Number 204254-98-8
  • Molecular Formula C14H23N3O4
  • Molecular Weight 297.36
Detailed View
Oseltamivir impurity 60

Oseltamivir impurity 60

  • CAT Number DCTI-C-001095
  • CAS Number 204255-04-9
  • Molecular Formula C14H24N4O3
  • Molecular Weight 296.37
Detailed View
Oseltamivir impurity 61

Oseltamivir impurity 61

  • CAT Number DCTI-C-001094
  • CAS Number 204255-06-1
  • Molecular Formula C16H26N4O4
  • Molecular Weight 338.41
Detailed View

Oseltamivir Impurity 64

  • CAT Number DCTI-C-002702
  • CAS NUMBER 651324-07-1
  • MOLECULAR FORMULA C26H44N2O4
  • MOLECULAR WEIGHT 448.65
Detailed View

Oseltamivir Impurity 73

  • CAT Number DCTI-C-002241
  • CAS NUMBER 220626-12-0
  • MOLECULAR FORMULA C10H16O7S
  • MOLECULAR WEIGHT 280.29
Detailed View
Oseltamivir Impurity 9 HCl

Oseltamivir Impurity 9 HCl

  • CAT Number DCTI-C-000133
  • CAS Number NA
  • Molecular Formula C22H37ClN2O4 (HCl Salt) C22H36N2O4 (Free base)
  • Molecular Weight 429.00 (HCl Salt) 392.54 (Free base)
Detailed View

Oseltamivir Impurity I. HCl

  • CAT Number DCTI-C-002242
  • CAS NUMBER 1052063-36-1 (free base)
  • MOLECULAR FORMULA C14H24N2O4 (Free base) ; C14H25ClN2O4 (HCl Salt)
  • MOLECULAR WEIGHT 284.36 (Free base) ; 320.81 (HCl Salt)
Detailed View
Oseltamivir Impurity VIII

Oseltamivir Impurity VIII

  • CAT Number DCTI-C-001201
  • CAS Number 312904-18-0
  • Molecular Formula C19H32N2O4
  • Molecular Weight 352.48
Detailed View
Oseltamivir Impurity-1

Oseltamivir Impurity-1

  • CAT Number DCTI-C-000587
  • CAS Number 2413185-87-0
  • Molecular Formula C22H32N2O6
  • Molecular Weight 420.51
Detailed View
Oseltamivir impurity-10

Oseltamivir impurity-10

  • CAT Number DCTI-C-000153
  • CAS Number NA
  • Molecular Formula C22H36N2O4
  • Molecular Weight 392.54
Detailed View

Oseltamivir Impurity-G

  • CAT Number DCTI-C-000198
  • CAS Number 956267-10-0
  • Molecular Formula C16H28N2O4 (Free Base); C16H29ClN2O4 (HCl Salt)
  • Molecular Weight 312.41 (Free Base); 348.87 (HCl Salt)
Detailed View

Oseltamivir Nitroso Impurity 1

  • CAT Number DCTI-C-002366
  • CAS NUMBER NA
  • MOLECULAR FORMULA C18H32N2O5
  • MOLECULAR WEIGHT 356.46
Detailed View

Oseltamivir Nitroso Impurity 2

  • CAT Number DCTI-C-002367
  • CAS NUMBER NA
  • MOLECULAR FORMULA C24H41N3O4
  • MOLECULAR WEIGHT 435.61
Detailed View

General Information

Oseltamivir Impurities and Oseltamivir

Daicel Pharma synthesizes high-quality Oseltamivir chiral isomers, (3R,4R,5R)- Oseltamivir hydrochloride, (3R,4S,5R)- Oseltamivir hydrochloride, ( 3S,4S,5S)-Oseltamivir hydrochloride, (3S,4R,5S)-Oseltamivir hydrochloride, (3S,4R,5R)-Oseltamivir hydrochloride, (3S,4S,5R)-Oseltamivir hydrochloride  (3R,4S,5S)-Oseltamivir hydrochloride. And other impurities like 1,2-Dihydro-Oseltamivir, Oseltamivir Carboxylic Acid, and more, which are crucial in the analysis of the quality, stability, and biological safety of the active pharmaceutical ingredient Oseltamivir. Moreover, Daicel Pharma offers custom synthesis of Oseltamivir impurities and delivers them globally.

Oseltamivir [CAS: 196618-13-0] is a synthetic antiviral prodrug converted to its active form in the liver for treating and preventing influenza A and B. It is a cyclohexene carboxylate ester derived from Oseltamivir acid, which slows down the spread of the influenza virus.

Oseltamivir: Use and Commercial Availability  

Oseltamivir is a medicine that treats acute and uncomplicated cases of influenza A or B illness in patients having symptoms for not more than two days. It is available under the trade names Oseltamivir Phosphate and Tamiflu.

Oseltamivir Structure and Mechanism of Action Oseltamivir Structure and Mechanism of Action

The chemical name of Oseltamivir is (3R,4R,5S)-4-acetylamino-5-amino-3(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester. Its chemical formula is C16H28N2O4, and its molecular weight is approximately 312.40 g/mol.

Oseltamivir inhibits influenza virus neuraminidase altering virus particle aggregation and release. It is an ethyl ester prodrug needing ester hydrolysis for conversion to oseltamivir carboxylate, its active form.

Oseltamivir Impurities and Synthesis

Oseltamivir impurities form during the synthetic process1 or storage of the drug. storage of the drug. They are related to hydrolysis, oxidation, and starting materials or reagents used in the process. These impurities can affect the potency and safety of the drug, so their levels need monitoring and control to ensure the quality of the final product.

Daicel offers a Certificate of Analysis (CoA) from a cGMP-compliant analytical facility for Oseltamivir impurity standards high-quality Oseltamivir chiral isomers, (3R,4R,5R)- Oseltamivir hydrochloride, (3R,4S,5R)- Oseltamivir hydrochloride, (3S,4S,5S)-Oseltamivir hydrochloride, (3S,4R,5S)-Oseltamivir hydrochloride, (3S,4R,5R)-Oseltamivir hydrochloride, (3S,4S,5R)-Oseltamivir hydrochloride (3R,4S,5S)-Oseltamivir hydrochloride. And other impurities like 1,2-Dihydro-Oseltamivir, Oseltamivir Carboxylic Acid, and more. The CoA includes complete characterization data, such as 1H NMR, 13C NMR, IR, MASS, and HPLC purity2. We also provide 13C-DEPT and CHN on request. We give a complete characterization report on delivery.

Daicel has the technology and expertise to prepare any unknown Oseltamivir impurity or degradation product. We also provide labeled compounds to quantify the efficacy of generic Oseltamivir. Daicel offers Oseltamivir -D5, Oseltamivir Carboxylic acid – D3 HCl, and Oseltamivir Hydrochloride-D3, deuterium labeled Oseltamivir compounds used in bio-analytical research, such as BA/BE studies.

References
FAQ's

References

  1. Willard Lew, Choung U. Kim, Hongtao LiuMatthew A. Williams, Carbocyclic compounds, Gilead Sciences, Inc, US5866601A, February 2, 1999
  2. Narasimhan, Balasubramanian; Abida, Khan; Srinivas, Kona, Stability indicating RP-HPLC method development and validation for oseltamivir API, Chemical & Pharmaceutical Bulletin, Volume: 56, Issue: 4, Pages: 413-417, 2008

Frequently Asked Questions

Reverse-phase high-performance liquid chromatography method helps detect and analyze the degradation impurities in Oseltamivir.

Impurities in Oseltamivir can affect the drug’s efficacy by decreasing its potency or interfering with its mechanism of action.

Acetonitrile or Methanol are the solvents used in analyzing many Oseltamivir impurities.

Oseltamivir impurities are stored at a controlled room temperature between 2-8 ⁰C or as indicated on the Certificate of Analysis (CoA).

Note: Products protected by valid patents by a manufacturer are not offered for sale in countries having patent protection. The sale of such products constitutes a patent infringement, and its liability is at the buyer's risk.

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