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Chemistry

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Also known as: 81-23-2, Decholin, Dehystolin, Felacrinos, Sanocholen, Dilabil
Molecular Formula
C24H34O5
Molecular Weight
402.5  g/mol
InChI Key
OHXPGWPVLFPUSM-KLRNGDHRSA-N
FDA UNII
NH5000009I

Dehydrocholic Acid
A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.
1 2D Structure

Dehydrocholic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
2.1.2 InChI
InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
2.1.3 InChI Key
OHXPGWPVLFPUSM-KLRNGDHRSA-N
2.1.4 Canonical SMILES
CC(CCC(=O)O)C1CCC2C1(C(=O)CC3C2C(=O)CC4C3(CCC(=O)C4)C)C
2.1.5 Isomeric SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(C(=O)C[C@H]3[C@H]2C(=O)C[C@H]4[C@@]3(CCC(=O)C4)C)C
2.2 Other Identifiers
2.2.1 UNII
NH5000009I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (5beta)-3,7,12-trioxocholan-24-oic Acid

2. Atrocholin

3. Cholan Hmb

4. Cholan-hmb

5. Cholanhmb

6. Chologon

7. Decholin

8. Dehydrocholate

9. Dehydrocholate, Sodium

10. Dehydrocholic Acid, Lithium Salt

11. Dehydrocholic Acid, Magnesium Salt

12. Dehydrocholic Acid, Potassium Salt

13. Dehydrocholic Acid, Sodium Salt

14. Ketocholanic Acid

15. Sodium Dehydrocholate

16. Triketocholanic Acid

17. Trioxocholate

2.3.2 Depositor-Supplied Synonyms

1. 81-23-2

2. Decholin

3. Dehystolin

4. Felacrinos

5. Sanocholen

6. Dilabil

7. Ketocholanic Acid

8. Chologon

9. Oxycholin

10. Procholon

11. Bilidren

12. Bilostat

13. Cholagon

14. Cholimed

15. Dehychol

16. Didrocolo

17. Drenobyl

18. Novocolin

19. Acolen

20. Dehycon

21. Didocol

22. Erebile

23. Hykolex

24. Triketocholanic Acid

25. Deidrocolico Vita

26. Biochol

27. Dehycol

28. Ketochol

29. Khologon

30. Dehydrocholate

31. Doxycholpotassium

32. Cholan Dh

33. Cholic Acid, Dehydro-

34. Dee-co

35. 3,7,12-trioxocholanic Acid

36. 3,7,12-triketocholanic Acid

37. 3,7,12-trioxo-5beta-cholanic Acid

38. Dehydrocholsaeure

39. 3,7,12-triketo-5beta-cholanoic Acid

40. Acide Dehydrocholique

41. 3,7,12-trioxo-5beta-cholan-24-oic Acid

42. Hydrochol

43. (4r)-4-[(5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic Acid

44. (5beta)-3,7,12-trioxocholan-24-oic Acid

45. Nsc-8796

46. Cholan-24-oic Acid, 3,7,12-trioxo-, (5.beta.)-

47. Mls000069501

48. 81-23-2 (acid)

49. Chebi:31459

50. Cholan-24-oic Acid, 3,7,12-trioxo-, (5b)-

51. Nh5000009i

52. (r)-4-((5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

53. Smr000058603

54. Dsstox_cid_2888

55. 3,7,12-trioxo-5.beta.-cholan-24-oic Acid

56. Dsstox_rid_76775

57. Dsstox_gsid_22888

58. Atrocholin

59. Cholepatin

60. Dehydrocholsaeure [german]

61. Acido Deidrocolico

62. Acido Deidrocolico [dcit]

63. Acido Dehidrocolico

64. Acido Dehidrocolico [spanish]

65. Acide Dehydrocholique [french]

66. Acidum Dehydrocholicum [latin]

67. Acidum Dehydrocholicum

68. Acido Dehidrocolico [inn-spanish]

69. Acide Dehydrocholique [inn-french]

70. Acidum Dehydrocholicum [inn-latin]

71. Nsc 8796

72. Einecs 201-335-7

73. Brn 3226734

74. Cholan-24-oic Acid, 3,7,12-trioxo-, (5beta)-

75. 5beta-cholanic Acid, 3,7,12-trioxo-

76. Dilahil

77. Dehydocholic Acid

78. 3,7,12-trioxo-5-beta-cholan-24-oic Acid

79. Unii-nh5000009i

80. Dehydro-ca

81. Dehydrocholate-acid

82. Ncgc00095777-01

83. Decholin (tn)

84. Prestwick_498

85. Cholan-24-oic Acid, 3,7,12-trioxo-, (5-beta)-

86. Mfcd00066410

87. Dehydrocholic Acid [usp:inn:ban:jan]

88. 3,7,12-trioxo-5beta-cholan-24-oicacid

89. Opera_id_1391

90. Prestwick3_000123

91. 3,12-trioxocholanic Acid

92. 5beta-cholan-24-oic Acid, 3,7,12-trioxo-

93. 3,12-triketocholanic Acid

94. 5-beta-cholan-24-oic Acid, 3,7,12-trioxo-

95. Schembl26391

96. Bspbio_000166

97. 4-10-00-03478 (beilstein Handbook Reference)

98. Mls001076501

99. Mls001424181

100. Bpbio1_000184

101. Chembl514446

102. Dehydrocholic Acid [mi]

103. Dehydrocholic Acid [inn]

104. Dehydrocholic Acid [jan]

105. Dtxsid2022888

106. Nsc8796

107. 3,7,12-trioxo-5-cholanic Acid

108. Dehydrocholic Acid [vandf]

109. Hms2052a11

110. Hms2095i08

111. Hms2235j07

112. Hms3712i08

113. Dehydrocholic Acid [mart.]

114. Dehydrocholic Acid [usp-rs]

115. Dehydrocholic Acid [who-dd]

116. Hy-b1393

117. Zinc3860869

118. 3,7,12-trioxo-24-cholanic Acid

119. Purified Dehydrocholic Acid (jp17)

120. Tox21_111519

121. Lmst04010106

122. Pdsp2_000076

123. S4562

124. 3,12-trioxo-5.beta.-cholanic Acid

125. Dehydrocholic Acid (jp17/usp/inn)

126. Dehydrocholic Acid, >=99.0% (t)

127. 3,12-triketo-5.beta.-cholanic Acid

128. Akos024284359

129. Tox21_111519_1

130. 3,12-triketo-5.beta.-cholanoic Acid

131. 5.beta.-cholanic Acid,7,12-trioxo-

132. Ccg-101103

133. Cs-4902

134. Db11622

135. Nc00353

136. 3,7,12-trioxo-5.beta.-cholanic Acid

137. 3,7,12-trioxocholan-24-oic Acid #

138. 3,7,12-triketo-5.beta.-cholanic Acid

139. Ncgc00024025-03

140. Ncgc00024025-05

141. 3,7,12-triketo-5.beta.-cholanoic Acid

142. 4-((1s,2s,7s,11s,10r,14r,15r)-2,15-dimethyl-5,9,16-trioxotetracyclo[8.7.0.0<2, 7>.0<11,15>]heptadec-14-yl)pentanoic Acid

143. Dehydrocholic Acid [usp Monograph]

144. 5.beta.-cholanic Acid, 3,7,12-trioxo-

145. 3,12-trioxo-5.beta.-cholan-24-oic Acid

146. 5.beta.-cholan-24-oic Acid,7,12-trioxo-

147. D0042

148. D01693

149. D94651

150. 3,7,12-tri-keto-5.beta.-cholan-24-oic Acid

151. 5.beta.-cholan-24-oic Acid, 3,7,12-trioxo-

152. Cholan-24-oic Acid,7,12-trioxo-, (5.beta.)-

153. Q903387

154. Sr-01000003022

155. Sr-01000003022-3

156. W-104212

157. Brd-k90976994-001-02-1

158. 3,7,12-trioxo-5beta-cholanic Acid 5beta-cholanic Acid-3,5,12-trione

159. Dehydrocholic Acid, United States Pharmacopeia (usp) Reference Standard

160. (r)-4-((5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoicacid

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 402.5 g/mol
Molecular Formula C24H34O5
XLogP32.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass402.24062418 g/mol
Monoisotopic Mass402.24062418 g/mol
Topological Polar Surface Area88.5 Ų
Heavy Atom Count29
Formal Charge0
Complexity756
Isotope Atom Count0
Defined Atom Stereocenter Count8
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

No approved therapeutic indications.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Following infusion of dehydrocholic acid (DHCA) in rats, the secretions of all the endogenous biliary bile acids were decreased within 30-60 minutes of infusion. Phospholipid secretion as well as cholesterol levels were also declined. The bile flow was increased after administration of dehydrocholic acid.


5.2 MeSH Pharmacological Classification

Cholagogues and Choleretics

Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic). (See all compounds classified as Cholagogues and Choleretics.)


5.3 Absorption, Distribution and Excretion

Absorption

The duodenal experiment indicates that dehydrocholic acid is absorbed from the proximal small intestine.


Route of Elimination

Administered dehydrocholic acid is excreted rapidly in bile as glycine- and taurine-conjugated bile acids.


Volume of Distribution

No pharmacokinetic data available.


Clearance

No pharmacokinetic data available.


5.4 Metabolism/Metabolites

The major site of metabolism is proposed to be the liver. The major metabolite accounting for 70% of total detectable metabolites is dihydroxymonoketo bile acid (3,7-dihydroxy-12-keto-5-cholanoic acid). About 20% of metabolites is monohydroxydiketoacid (3-hydroxy-7,12-keto-5-cholanoic acid) and about 10% is cholic acid.


5.5 Biological Half-Life

No pharmacokinetic data available.


5.6 Mechanism of Action

It is proposed that dehydrocholic acid induces choleresis, which is associated with biliary lipid secretion and reduced secretion of endogenous and/or exogenous biliary components. Dehydrocholic acid may decrease bile phospholipid secretion due to a lack of micelle formation by dehydrocholic acid-produced bile. A study suggests that due to enhanced permeability of tight junctions in the canalicular membranes, dehydrocholic acid facilitates direct exchange between bile and plasma.


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Excipient Market Overview: Roquette, Seqens, Evonik make strategic moves; new guidelines deal with contamination
The pharmaceutical industry has long recognized the critical role excipients or inactive ingredients play in drug formulation and delivery. Excipients can comprise up to 90 percent of a medicine's total ingredients and serve crucial functions as binders, disintegrants, coatings, preservatives, colors, and flavorings. According to recent market research, the pharmaceutical excipients market was valued at US$ 9.27 billion in 2023. It is growing at a compound annual growth rate (CAGR) of 7.03 percent and is projected to reach US$ 18.48 billion by 2032. The main factors driving market growth is an increased demand for multifunctional excipients, coupled with the expanding use of generic medications. The development in the biologics sector and advancements in nanotechnology are also contributing significantly to market growth. Major excipient providers include BASF, Evonik, Merck KGaA owned MilliporeSigma, Gangwal Healthcare, Roquette Frères, DuPont, Croda International, Seqens, Boai NKY Pharmaceuticals, PMC Isochem, Minakem, Kewpie Corporation, Ashland Global, SPI Pharma, Pfanstiehl, Nanjing Well Pharmaceutical, ICE Pharma, Anhui Ribobay Pharmaceutical and Nippon Fine Chemical.  View Our Dashboard on Major Excipient Companies in 2024 (Free Excel Available) WHO, India’s CDSCO tighten regulations; new GMP guidelines implemented to curb contamination Last year, the World Health Organization (WHO) issued a health alert linking at least 300 child deaths in the Gambia, Uzbekistan, and Indonesia to the ingestion of contaminated cough syrups containing unacceptable levels of diethylene glycol (DEG) and ethylene glycol (EG). In response to the tragic events, the WHO released two draft appendices to its guideline on good manufacturing practices (GMPs) for excipients this year. Manufacturers are now required to use suitable risk assessment tools to identify and mitigate potential hazards.  Since India-made cough syrups had been linked to the deaths, India’s drug regulator — Central Drugs Standard Control Organization (CDSCO) — took steps to prevent contamination, and advised drugmakers to only use pharmaceutical-grade excipients from approved sources. Furthermore, the Indian Health Ministry proposed amendments to the Drugs and Cosmetics Rules, 1945 to include details of excipients on drug labels. While listing all excipients on every strip of medicine may be challenging, the ministry suggested mentioning those causing hypersensitivity on the label. Applicants now mandatorily need to submit evidence of stability and safety of excipients. These regulatory developments have significant implications for excipient manufacturers and pharmaceutical companies worldwide. Leading pharmaceutical excipient firms like Gangwal Healthcare, Sigachi Industries, and Nitika Pharmaceuticals are well-positioned to meet these heightened quality and safety standards, given their long-standing commitment to producing high-quality, compliant excipients.  View Our Dashboard on Major Excipient Companies in 2024 (Free Excel Available)   Roquette buys IFF’s pharma unit for US$ 2.85 bn; Evonik opens new spray-drying facility in Darmstadt In a significant industry move, France-based Roquette entered into an agreement to acquire IFF's pharma solutions business in a deal valued at US$ 2.85 billion. This acquisition is set to rebalance family-owned Roquette’s portfolio around health and nutrition. The deal is expected to accelerate Roquette’s growth and significantly strengthen its presence in the excipients market. Evonik has opened a new facility for drying aqueous dispersions of its Eudragit polymers at its site in Darmstadt, Germany. The facility will help Evonik meet increasing demand from drugmakers for its oral drug delivery solutions. The plant uses green energy solutions. The company has also partnered University of Mainz to commercialize a new class of polyethylene glycols (PEG) lipids for nucleic acid delivery. Evonik’s Health Care business has been growing its nucleic acid drug and vaccine delivery portfolio.  Germany’s Johannes Gutenberg University of Mainz was the first to develop randomized polyethylene glycols (rPEGs). This collaboration aims to expand Evonik’s toolbox of technologies for nucleic acid-based medicines, offering an improved immunogenicity profile for lipid nanoparticle carriers used in mRNA vaccines and therapeutics. Asahi Kasei made significant strides in addressing a pressing industry concern that emerged in 2018 when potentially carcinogenic nitrosamine impurities were detected in several pharmaceuticals. Guided by regional authorities, such as the European Medicines Agency and the US Food and Drug Administration, the pharmaceutical industry has been carrying out extensive assessments and research to identify the cause of these impurities. In response to this challenge, Asahi Kasei developed its Ceolus microcrystalline cellulose with extremely low nitrite levels. The Japanese company achieved nitrite concentrations of 0.1 micrograms per gram or less, which is equivalent to 0.1 parts per million (ppm). The company also started full commercial operation of its second manufacturing facility for Ceolus in Japan, enhancing supply capacity and stability. JRS Pharma and Gujarat Microwax opened a state-of-the-art cotton-based croscarmellose sodium plant in Mehsana, Gujarat (India). This facility aims to produce high-quality excipients that meet global standards, potentially reducing India's dependency on imports and boosting its presence in the global excipient market. The Indian excipient industry accounts for less than 1 percent of the global market share.  View Our Dashboard on Major Excipient Companies in 2024 (Free Excel Available)   Seqens to advance innovative polymer; biologics, personalized medicine create demand for specialized excipients Recent industry collaborations highlight the ongoing innovation in novel excipients. France’s Seqens, with over 20 years of polymer development experience, was chosen by Pleryon Therapeutics to advance its leading osteoarthritis candidate – an innovative GMP polymer. This collaboration leverages Seqens’ newly expanded and modernized cGMP plant in Aramon, France, demonstrating the industry’s commitment to investing in advanced manufacturing capabilities for novel excipients.  The rise of biologics and personalized medicine has created a demand for specialized excipients capable of stabilizing complex molecules and enabling targeted drug delivery. Roquette’s launch of Lycagel Flex, a hydroxypropyl pemix for nutraceutical and pharmaceutical softgel capsules, exemplifies this trend. Built on Roquette’s market-first Lycagel pea starch technology, this plant-based alternative to gelatin offers manufacturers the flexibility to customize formulations for a range of production and end-user needs. The innovative pea starch foundation also underscores the industry’s move towards sustainable bio-based excipients. The trend towards patient-centric drug development has also influenced excipient innovation. Excipients that can improve palatability, ease of swallowing, or enable novel dosage forms (such as orally disintegrating tablets) are in high demand. For example, IFF brought a super disintegrant Ac-Di-Sol, that supports faster disintegration and drug dissolution in oral disintegrating tablets, improving patient experience.  View Our Dashboard on Major Excipient Companies in 2024 (Free Excel Available)   Our view The heightened regulatory scrutiny on excipients due to product contamination incidents has created a high risk perception and uncertainty around the regulatory acceptance of novel excipients. That said, novel excipients are central to the development of new drug modalities and therapies. Going forward, sustainability will also become an increasingly important factor in excipient selection and development. As the industry innovates towards biologics, personalized therapies, and patient-centric formulations, the role of high-quality, multifunctional excipients will only grow more vital in ensuring drug stability, bioavailability, and patient compliance. Companies that can navigate the complex regulatory landscape, invest in R&D, and offer high-quality, multifunctional excipients will be well-positioned to succeed in this evolving market.   

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https://www.pharmacompass.com/radio-compass-blog/excipient-market-overview-roquette-seqens-evonik-make-strategic-moves-new-guidelines-deal-with-contamination

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API | Excipient name

Dehydrocholic Acid

Synonyms

81-23-2, Decholin, Dehystolin, Felacrinos, Sanocholen, Dilabil

Cas Number

81-23-2

Unique Ingredient Identifier (UNII)

NH5000009I

About Dehydrocholic Acid

A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.

Acolen Manufacturers

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

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

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Acolen GMP

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

Acolen CoA

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

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

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