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Chemistry

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Also known as: 50370-12-2, Cefadroxil anhydrous, Cephadroxil, Cefadroxilo, Cefadroxilum, D-cefadroxil
Molecular Formula
C16H17N3O5S
Molecular Weight
363.4  g/mol
InChI Key
BOEGTKLJZSQCCD-UEKVPHQBSA-N
FDA UNII
Q525PA8JJB

Cefadroxil
Long-acting, broad-spectrum, water-soluble, CEPHALEXIN derivative.
Cefadroxil anhydrous is a Cephalosporin Antibacterial.
1 2D Structure

Cefadroxil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
2.1.2 InChI
InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1
2.1.3 InChI Key
BOEGTKLJZSQCCD-UEKVPHQBSA-N
2.1.4 Canonical SMILES
CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)SC1)C(=O)O
2.1.5 Isomeric SMILES
CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)SC1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
Q525PA8JJB
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4 Hydroxycephalexin

2. 4-hydroxycephalexin

3. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6r-(6alpha,7beta(r*)))-

4. Bidocef

5. Bl S 578

6. Bl S578

7. Bl-s 578

8. Bl-s578

9. Bls 578

10. Bls578

11. Cefadroxil Anhydrous

12. Cefadroxil Monohydrate

13. Cephadroxyl

14. Duricef

15. S 578

16. S-578

17. S578

18. Ultracef

2.3.2 Depositor-Supplied Synonyms

1. 50370-12-2

2. Cefadroxil Anhydrous

3. Cephadroxil

4. Cefadroxilo

5. Cefadroxilum

6. D-cefadroxil

7. Cefadroxil [inn]

8. Bl-s578

9. Anhydrous Cefadroxil

10. Chebi:3479

11. (6r,7r)-7-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

12. (6r,7r)-7-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

13. Bl-s 578

14. Cdx

15. Q525pa8jjb

16. Duracef

17. Nsc-756664

18. Dsstox_cid_2749

19. Dsstox_rid_76714

20. Dsstox_gsid_22749

21. Mjf-11567-3

22. (6r,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

23. Cefadroxil (as Monohydrate)

24. Cefadroxilum [inn-latin]

25. Cefadroxilo [inn-spanish]

26. (6r,7r)-7-[(2r)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

27. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2r)-amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6r,7r)-

28. Sumacef (tn)

29. Cefadroxil/cefadroxil Hemihydrate

30. S 578

31. S-578

32. Unii-q525pa8jjb

33. Cefradroxil

34. Cefadrops

35. Ncgc00016858-01

36. (6r,7r)-7-(((2r)-2-amino-2-(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

37. Einecs 256-555-6

38. Cas-50370-12-2

39. Cefadroxil, Anhydrous

40. Cefadroxil (jp17)

41. Spectrum_000104

42. Cefadroxil [mi]

43. Cefadroxil [jan]

44. (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

45. Prestwick0_000434

46. Prestwick1_000434

47. Prestwick2_000434

48. Prestwick3_000434

49. Spectrum2_000087

50. Spectrum4_000266

51. Spectrum5_000663

52. Epitope Id:117131

53. Cefadroxil [who-dd]

54. Chembl1644

55. Bspbio_000448

56. Kbiogr_000732

57. Kbioss_000544

58. (6r,7r)-7-((r)-2-amino-2-(p-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

59. Mls002207219

60. Divk1c_000409

61. Schembl151320

62. Spbio_000014

63. Spbio_002387

64. Cefadroxil, Analytical Standard

65. Bpbio1_000494

66. Gtpl4831

67. Dtxsid8022749

68. Hms501e11

69. Kbio1_000409

70. Kbio2_000544

71. Kbio2_003112

72. Kbio2_005680

73. Ninds_000409

74. Hms1569g10

75. Hms2096g10

76. Hms3713g10

77. Pharmakon1600-01500163

78. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2r)-2-amino-2-(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6r,7r)-

79. Hy-b1190

80. Zinc3830391

81. Tox21_110651

82. Bbl033696

83. Bdbm50350467

84. Mfcd00865091

85. Nsc756664

86. Stk801939

87. Akos005622555

88. Tox21_110651_1

89. Ccg-220434

90. Cs-4696

91. Db01140

92. Idi1_000409

93. Ncgc00179556-01

94. Ncgc00179556-03

95. As-11655

96. Smr001306770

97. Cefprozil Impurity B [ep Impurity]

98. Sbi-0051305.p003

99. Ab00513838

100. Cefprozil E Impurity B [ep Impurity]

101. C-2462

102. C06878

103. D00257

104. D81830

105. 592c878

106. Q2319020

107. Cefprozil Monohydrate Impurity B [ep Impurity]

108. Cefadroxil Monohydrate, Antibiotic For Culture Media Use Only

109. (7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

110. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6r-(6-alpha,7-beta(r*)))-

111. 7beta-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-3,4-didehydrocepham-4-carboxylic Acid

2.4 Create Date
2005-07-11
3 Chemical and Physical Properties
Molecular Weight 363.4 g/mol
Molecular Formula C16H17N3O5S
XLogP3-2.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass363.08889182 g/mol
Monoisotopic Mass363.08889182 g/mol
Topological Polar Surface Area158 Ų
Heavy Atom Count25
Formal Charge0
Complexity629
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameCefadroxil
PubMed HealthCefadroxil (By mouth)
Drug ClassesAntibiotic
Drug LabelCefadroxil monohydrate, USP is a semisynthetic cephalosporin antibiotic intended for oral administration. It is a white to yellowish-white crystalline powder. It is soluble in water and it is acid-stable. It is chemically designated as 5-Thia-1- azab...
Active IngredientCefadroxil/cefadroxil hemihydrate
Dosage FormTablet; Capsule; For suspension
RouteOral
Strengtheq 250mg base/5ml; eq 500mg base; eq 125mg base/5ml; eq 500mg base/5ml; eq 1gm base
Market StatusPrescription
CompanyRanbaxy; Teva Pharms; Aurobindo; Aurobindo Pharma; Lupin; Sandoz; Hikma Pharms; Orchid Hlthcare; Hikma

2 of 2  
Drug NameCefadroxil
PubMed HealthCefadroxil (By mouth)
Drug ClassesAntibiotic
Drug LabelCefadroxil monohydrate, USP is a semisynthetic cephalosporin antibiotic intended for oral administration. It is a white to yellowish-white crystalline powder. It is soluble in water and it is acid-stable. It is chemically designated as 5-Thia-1- azab...
Active IngredientCefadroxil/cefadroxil hemihydrate
Dosage FormTablet; Capsule; For suspension
RouteOral
Strengtheq 250mg base/5ml; eq 500mg base; eq 125mg base/5ml; eq 500mg base/5ml; eq 1gm base
Market StatusPrescription
CompanyRanbaxy; Teva Pharms; Aurobindo; Aurobindo Pharma; Lupin; Sandoz; Hikma Pharms; Orchid Hlthcare; Hikma

4.2 Drug Indication

For the treatment of the following infections (skin, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staphylococci and Streptococcus pyogenes


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CEFADROXIL ANHYDROUS
5.3.2 FDA UNII
Q525PA8JJB
5.3.3 Pharmacological Classes
Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
5.4 ATC Code

J01DB05

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DB - First-generation cephalosporins

J01DB05 - Cefadroxil


5.5 Absorption, Distribution and Excretion

Absorption

Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.


Route of Elimination

Over 90% of the drug is excreted unchanged in the urine within 24 hours. Cefadroxil was detected in the placenta and breast milk.


5.6 Biological Half-Life

1.5 hours


5.7 Mechanism of Action

Like all beta-lactam antibiotics, cefadroxil binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefadroxil interferes with an autolysin inhibitor.


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20-Jan-2021
20-Feb-2025
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Looking for 66592-87-8 / Cefadroxil API manufacturers, exporters & distributors?

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PharmaCompass offers a list of Cefadroxil API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Cefadroxil manufacturer or Cefadroxil supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Cefadroxil manufacturer or Cefadroxil supplier.

PharmaCompass also assists you with knowing the Cefadroxil API Price utilized in the formulation of products. Cefadroxil API Price is not always fixed or binding as the Cefadroxil Price is obtained through a variety of data sources. The Cefadroxil Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Cefadroxil

Synonyms

50370-12-2, Cefadroxil anhydrous, Cephadroxil, Cefadroxilo, Cefadroxilum, D-cefadroxil

Cas Number

66592-87-8

Unique Ingredient Identifier (UNII)

Q525PA8JJB

About Cefadroxil

Long-acting, broad-spectrum, water-soluble, CEPHALEXIN derivative.

Ultracef Manufacturers

A Ultracef manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Ultracef, including repackagers and relabelers. The FDA regulates Ultracef manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Ultracef API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Ultracef manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Ultracef Suppliers

A Ultracef supplier is an individual or a company that provides Ultracef active pharmaceutical ingredient (API) or Ultracef finished formulations upon request. The Ultracef suppliers may include Ultracef API manufacturers, exporters, distributors and traders.

click here to find a list of Ultracef suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Ultracef USDMF

A Ultracef DMF (Drug Master File) is a document detailing the whole manufacturing process of Ultracef active pharmaceutical ingredient (API) in detail. Different forms of Ultracef DMFs exist exist since differing nations have different regulations, such as Ultracef USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Ultracef DMF submitted to regulatory agencies in the US is known as a USDMF. Ultracef USDMF includes data on Ultracef's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Ultracef USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Ultracef suppliers with USDMF on PharmaCompass.

Ultracef KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Ultracef Drug Master File in Korea (Ultracef KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Ultracef. The MFDS reviews the Ultracef KDMF as part of the drug registration process and uses the information provided in the Ultracef KDMF to evaluate the safety and efficacy of the drug.

After submitting a Ultracef KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Ultracef API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Ultracef suppliers with KDMF on PharmaCompass.

Ultracef CEP

A Ultracef CEP of the European Pharmacopoeia monograph is often referred to as a Ultracef Certificate of Suitability (COS). The purpose of a Ultracef CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Ultracef EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Ultracef to their clients by showing that a Ultracef CEP has been issued for it. The manufacturer submits a Ultracef CEP (COS) as part of the market authorization procedure, and it takes on the role of a Ultracef CEP holder for the record. Additionally, the data presented in the Ultracef CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Ultracef DMF.

A Ultracef CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Ultracef CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Ultracef suppliers with CEP (COS) on PharmaCompass.

Ultracef WC

A Ultracef written confirmation (Ultracef WC) is an official document issued by a regulatory agency to a Ultracef manufacturer, verifying that the manufacturing facility of a Ultracef active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Ultracef APIs or Ultracef finished pharmaceutical products to another nation, regulatory agencies frequently require a Ultracef WC (written confirmation) as part of the regulatory process.

click here to find a list of Ultracef suppliers with Written Confirmation (WC) on PharmaCompass.

Ultracef NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Ultracef as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Ultracef API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Ultracef as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Ultracef and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Ultracef NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Ultracef suppliers with NDC on PharmaCompass.

Ultracef GMP

Ultracef Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Ultracef GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Ultracef GMP manufacturer or Ultracef GMP API supplier for your needs.

Ultracef CoA

A Ultracef CoA (Certificate of Analysis) is a formal document that attests to Ultracef's compliance with Ultracef specifications and serves as a tool for batch-level quality control.

Ultracef CoA mostly includes findings from lab analyses of a specific batch. For each Ultracef CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Ultracef may be tested according to a variety of international standards, such as European Pharmacopoeia (Ultracef EP), Ultracef JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Ultracef USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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