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Synopsis

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Chemistry

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Also known as: 73573-88-3, Compactin, Ec 700-442-0, Ml-236b, Mevastatin [inn], Mevastatina
Molecular Formula
C23H34O5
Molecular Weight
390.5  g/mol
InChI Key
AJLFOPYRIVGYMJ-INTXDZFKSA-N
FDA UNII
1UQM1K0W9X

Mevastatin
Mevastatin is an HMG-CoA reductase inhibitor that was initially isolated from the mold Pythium ultimum. Mevastatin was the first statin to enter clinical trials.
1 2D Structure

Mevastatin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
2.1.2 InChI
InChI=1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
2.1.3 InChI Key
AJLFOPYRIVGYMJ-INTXDZFKSA-N
2.1.4 Canonical SMILES
CCC(C)C(=O)OC1CCC=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O
2.1.5 Isomeric SMILES
CC[C@H](C)C(=O)O[C@H]1CCC=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O
2.2 Other Identifiers
2.2.1 UNII
1UQM1K0W9X
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6-demethylmevinolin

2. Compactin

3. Cs 500

4. Ml 236b

5. Ml-236b

6. Ml236b

2.3.2 Depositor-Supplied Synonyms

1. 73573-88-3

2. Compactin

3. Ec 700-442-0

4. Ml-236b

5. Mevastatin [inn]

6. Mevastatina

7. Mevastatine

8. Mevastatinum

9. Mevastatinum [inn-latin]

10. Antibiotic Ml 236b

11. Cs 500

12. Ml 236 B

13. [(1s,7s,8s,8ar)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2s)-2-methylbutanoate

14. 1uqm1k0w9x

15. Mevastatin (compactin)

16. Chembl54440

17. Chebi:34848

18. Ml236b

19. Nsc-759322

20. (1s,7s,8s,8ar)-1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-((2r,4r)-tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl)ethyl)-1-naphthyl (s)-2-methylbutyrate

21. Compactin (penicillium)

22. Mevastatine [inn-french]

23. Mevastatina [inn-spanish]

24. (1s,7s,8s,8ar)-8-(2-((2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (s)-2-methylbutanoate

25. (s)-((1s,7s,8s,8ar)-8-(2-((2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate

26. Butanoic Acid, 2-methyl-, (1s,7s,8s,8ar)-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-[(2r,4r)-tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl]ethyl]-1-naphthalenyl Ester, (2s)-

27. Smr000336944

28. Ccris 4505

29. Unii-1uqm1k0w9x

30. Kompaktin

31. Ncgc00095942-01

32. Mevastatin- Bio-x

33. Mfcd05662341

34. Mevastatin [mi]

35. Mevastatin [jan]

36. Mevastatin [mart.]

37. Schembl1116

38. Dsstox_cid_20684

39. Dsstox_rid_79540

40. Mevastatin [usp-rs]

41. Dsstox_gsid_40684

42. Lopac0_000754

43. Mls000721804

44. Mls000759452

45. Mls001424284

46. Mls002207227

47. Gtpl3031

48. Dtxsid4040684

49. Mevastatin, >=96% (hplc)

50. Hms2052p07

51. Hms2089d10

52. Hms2232n09

53. Hms3262g10

54. Hms3268a19

55. Hms3412h15

56. Hms3676h15

57. Hms3713b06

58. Zinc3833876

59. Tox21_111540

60. Tox21_500754

61. Bdbm50011036

62. Cs-500

63. Nsc779705

64. S4223

65. Akos015994712

66. Mevastatin, >=95% (hplc), Powder

67. Ccg-101174

68. Cs-1234

69. Db06693

70. Ks-1085

71. Lp00754

72. Nc00424

73. Nsc 759322

74. Nsc-779705

75. Sdccgsbi-0050732.p002

76. 7-(1,2,6,7,8,8a-hexahydro-2-methyl-8-(2-methylbutyryloxy)naphthyl)-3-hydroxyheptan-5-olide

77. Smp1_000077

78. Ncgc00025202-04

79. Ncgc00261439-01

80. (1s,7s,8s,8ar)-8-(2-((2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl(2s)-2-methylbutanoate

81. Bm164666

82. Butanoic Acid, 2-methyl-, (1s,7s,8s,8ar)-1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl)ethyl)-1-naphthalenyl Ester, (2s)-

83. Butanoic Acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl)ethyl)-1-naphthalenyl Ester, (1s-(1-alpha(r*),7-beta,8-beta(2s*,4s*),8a-beta))-

84. Hy-17408

85. Mevastatin 100 Microg/ml In Acetonitrile

86. Cas-73573-88-3

87. Lovastatin Impurity A [ep Impurity]

88. B1788

89. Eu-0100754

90. M2275

91. H11997

92. M 2537

93. Ab00588266-06

94. Ab00588266-08

95. Ab00588266_09

96. 573m883

97. A837861

98. Q414407

99. Sr-01000729493

100. L-637312

101. Sr-01000729493-4

102. Brd-k94441233-001-03-1

103. Brd-k94441233-001-17-1

104. (1s,7s,8s,8ar)-8-{2-[(2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2s)-2-methylbutanoate

105. (s)-((1s,7s,8s,8ar)-8-(2-((2r,4r)-4-hydroxy-6-oxo-tetrahydro-2h-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate

106. (s)-2-methyl-butyric Acid (1s,7s,8s,8ar)-8-[2-((2r,4r)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester

107. 2-methyl-butyric Acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester

108. 2-methyl-butyric Acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester((+)-compactin)

109. 2-methyl-butyric Acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester(compactin)

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 390.5 g/mol
Molecular Formula C23H34O5
XLogP33.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count7
Exact Mass390.24062418 g/mol
Monoisotopic Mass390.24062418 g/mol
Topological Polar Surface Area72.8 Ų
Heavy Atom Count28
Formal Charge0
Complexity637
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Not used therapeutically due to its many side effects.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The primary cause of cardiovascular disease is atherosclerotic plaque formation. Mevastatin lowers hepatic production of cholesterol to reduce the risk of cardiovascular disease. Mevastatin competitively inhibits HMG-CoA reductase. This inhibition prevents the rate limiting step in cholesterol synthesis. Decreased hepatic cholesterol levels causes increased uptake of low density lipoprotein (LDL) cholesterol and reduces cholesterol levels in the circulation.


5.2 MeSH Pharmacological Classification

Anticholesteremic Agents

Substances used to lower plasma cholesterol levels. (See all compounds classified as Anticholesteremic Agents.)


Anti-Bacterial Agents

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


Hydroxymethylglutaryl-CoA Reductase Inhibitors

Compounds that inhibit HYDROXYMETHYLGLUTARYL COA REDUCTASES. They have been shown to directly lower CHOLESTEROL synthesis. (See all compounds classified as Hydroxymethylglutaryl-CoA Reductase Inhibitors.)


Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)


5.3 Mechanism of Action

Mevastatin is structurally similar to the HMG, a substituent of the endogenous substrate of HMG-CoA reductase. Mevastatin is a prodrug that is activated in vivo via hydrolysis of the lactone ring. The hydrolyzed lactone ring mimics the tetrahedral intermediate produced by the reductase allowing the agent to bind with 10,000 times greater affinity than its natural substrate. The bicyclic portion of mevastatin binds to the coenzyme A portion of the active site.


REF. STANDARDS & IMPURITIES

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ABOUT THIS PAGE

Mevastatin Manufacturers

A Mevastatin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Mevastatin, including repackagers and relabelers. The FDA regulates Mevastatin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Mevastatin 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 Mevastatin manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Mevastatin Suppliers

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

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

Mevastatin USDMF

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

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

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

Mevastatin 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 Mevastatin as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Mevastatin 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 Mevastatin 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 Mevastatin and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Mevastatin NDC to their finished compounded human drug products, they may choose to do so.

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

Mevastatin GMP

Mevastatin 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 Mevastatin 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 Mevastatin GMP manufacturer or Mevastatin GMP API supplier for your needs.

Mevastatin CoA

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

Mevastatin CoA mostly includes findings from lab analyses of a specific batch. For each Mevastatin 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.

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