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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Tetralysal, N-lysinomethyltetracycline, Limeciclina, Lymecyclinum, Tetracycline-l-methylenelysine, Ciclolysal
Molecular Formula
C29H38N4O10
Molecular Weight
602.6  g/mol
InChI Key
PZTCVADFMACKLU-UEPZRUIBSA-N
FDA UNII
7D6EM3S13P

Lymecycline
A semisynthetic antibiotic related to TETRACYCLINE. It is more readily absorbed than TETRACYCLINE and can be used in lower doses.
1 2D Structure

Lymecycline

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-6-[[[(4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carbonyl]amino]methylamino]-2-aminohexanoic acid
2.1.2 InChI
InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34-35,38,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1
2.1.3 InChI Key
PZTCVADFMACKLU-UEPZRUIBSA-N
2.1.4 Canonical SMILES
CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)NCNCCCCC(C(=O)O)N)N(C)C)O
2.1.5 Isomeric SMILES
C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)NCNCCCC[C@@H](C(=O)O)N)N(C)C)O
2.2 Other Identifiers
2.2.1 UNII
7D6EM3S13P
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hydrochloride, Lymecycline

2. Lymecycline Hydrochloride

3. Lysine, Tetracycline-l-methylene

4. Lysine, Tetracyclinemethylene

5. N Lysinomethyltetracycline

6. N-lysinomethyltetracycline

7. Tetracycline L Methylene Lysine

8. Tetracycline-l-methylene Lysine

9. Tetracyclinemethylene Lysine

2.3.2 Depositor-Supplied Synonyms

1. Tetralysal

2. N-lysinomethyltetracycline

3. Limeciclina

4. Lymecyclinum

5. Tetracycline-l-methylenelysine

6. Ciclolysal

7. Mucomycin

8. 992-21-2

9. Tetracycline-l-methylene Lysine

10. Ciclolysine

11. Tetracyclinemethylenelysine

12. Lymecycline (inn)

13. (+)-n-(5-amino-5-carboxypentylaminomethyl)-4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxonaphthacene-2-carboxamide

14. Tetralisal

15. 7d6em3s13p

16. N6-((4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamido)methyl)lysine

17. Chebi:59040

18. N(2)-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline

19. Lymecycline [inn]

20. L-lysine,n6-[[[[(4s,4as,5as,6s,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl]carbonyl]amino]methyl]-

21. N(6)-[({[(4s,4as,5as,6s,12as)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]carbonyl}amino)methyl]-l-lysine

22. Infaciclina

23. Lisinbiotic

24. Vebicyclysal

25. Ciclisin

26. Armyl

27. Tetraciclina-l-metilenlisina

28. (2s)-6-[[[(4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carbonyl]amino]methylamino]-2-aminohexanoic Acid

29. Lymecycline [inn:ban]

30. Lymecyclinum [inn-latin]

31. Limeciclina [inn-spanish]

32. Tetracycline, Lysinomethyl-

33. Unii-7d6em3s13p

34. Einecs 213-592-2

35. Tetraciclina-l-metilenlisina [italian]

36. Lymecycline (85%)

37. Lymecycline [mi]

38. Lymecycline [mart.]

39. Lymecycline [who-dd]

40. Schembl149162

41. Tetracycline-l Methylene-lysine

42. Chembl2103929

43. Schembl23248015

44. Gtpl10912

45. Lymecycline [ep Monograph]

46. N(sup 2)-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline

47. Zinc53682936

48. Akos016340328

49. Db00256

50. Ks-1366

51. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, Lysinemethylene Deriv.

52. D06884

53. Q897051

54. N2-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline

55. L-lysine, N6-(((((4s,4as,5as,6s,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl)carbonyl)amino)methyl)-

56. L-lysine, N6-((((4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl)carbonyl)amino)methyl)-, (4s-(4alpha,4aalpha,6beta,12aalpha))-

57. Lysine, N(sup 6)-((4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamido)methyl)-, (+)-

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 602.6 g/mol
Molecular Formula C29H38N4O10
XLogP3-4.4
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count13
Rotatable Bond Count10
Exact Mass602.25879342 g/mol
Monoisotopic Mass602.25879342 g/mol
Topological Polar Surface Area243 Ų
Heavy Atom Count43
Formal Charge0
Complexity1230
Isotope Atom Count0
Defined Atom Stereocenter Count6
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

Lymecycline is used for the treatment of acne in addition to other susceptible infections; propionibacterium is often the cause of acne. Some of the infections that can be treated with lymecycline include upper respiratory tract infections, urinary tract infections, bronchitis, chlamydial infections, and rickettsial infections.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Lymecycline, like other tetracyclines, exerts bacteriostatic actions on intracellular and extracellular bacteria, treating susceptible bacterial infections. It has been shown to be safe and effective in the treatment of moderate to severe acne. It is important to note that like other tetracyclines, lymecycline may cause esophageal irritation and ulceration, which can be prevented by drinking adequate fluids during administration. It also has the potential to cause photosensitivity. Lymecycline can lead to renal tubular acidosis or hepatic toxicity. It is not recommended to administer this drug in patients with renal disease or severe hepatic disease.


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 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01A - Tetracyclines

J01AA - Tetracyclines

J01AA04 - Lymecycline


5.4 Absorption, Distribution and Excretion

Absorption

Lymecycline is 77-88% absorbed after oral administration with a relative bioavailability of 70%. The Cmax of lymecycline is 2.1 mg/L and is achieved about 3 hours after administration. The AUC is 21.9 4.3 mgh/L.


Route of Elimination

Lymecycline is 25% eliminated in the urine. Based on being a member of the tetracycline drug class, fecal elimination is likely another route of elimination.


Volume of Distribution

Lymecycline is lipophilic and easily crosses the cell membrane and passively diffuses through bacterial porin channels. As a second-generation tetracycline, the concentration in the bile ranges from 10 to 25 times higher than plasma concentration. In general, the volume of distribution of tetracyclines ranges from 1.31.7 L/kg or 100130 L.


Clearance

Lymecycline is partially cleared by the kidneys, like other tetracyclines.


5.5 Biological Half-Life

The half-life of lymecycline is approximately 8 hours.


5.6 Mechanism of Action

Normally, the ribosome synthesizes proteins through the binding of aminoacyl-tRNA to the mRNA-ribosome complex. Lymecycline binds to the 30S ribosomal subunit, preventing amino-acyl tRNA from binding to the A site of the ribosome, which prevents the elongation of polypeptide chains. This results in bacteriostatic actions, treating various infections.


CEP/COS

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R1-CEP 2010-239 - Rev 02
Valid
Chemical
2023-02-09
1654
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Certificate Number : R1-CEP 2010-239 - Rev 02

Status : Valid

Issue Date : 2023-02-09

Type : Chemical

Substance Number : 1654

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Certificate Number : CEP 2020-040 - Rev 01

Status : Valid

Issue Date : 2024-12-18

Type : Chemical

Substance Number : 1654

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Certificate Number : R0-CEP 2023-172 - Rev 00

Status : Valid

Issue Date : 2023-08-09

Type : Chemical

Substance Number : 1654

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Certificate Number : R1-CEP 2016-186 - Rev 01

Status : Valid

Issue Date : 2023-04-26

Type : Chemical

Substance Number : 1654

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Lymecycline EP/BP/IH

Date of Issue : 2022-12-16

Valid Till : 2025-12-15

Written Confirmation Number : WC-0544

Address of the Firm : Plot No. 825,826,827, Industrial Area, Sector-Ill, Pithampur, Dhar-454774, Madhy...

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Kopran

India
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Kopran

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Lymecycline BP/Ph. Eur.

Date of Issue : 2022-08-31

Valid Till : 2025-07-14

Written Confirmation Number : WC-0090

Address of the Firm : MIs Kopran Research Laboratories Limited, K-4/4, Additional MIDC, Birwadi, Mahad...

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Suanfarma

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Lymecycline

About the Company : Suanfarma founded in 1993, is a B2B life science partner committed to health advancement by developing, manufacturing, & distributing high-quality APIs for the pharmaceutical indus...

Suanfarma founded in 1993, is a B2B life science partner committed to health advancement by developing, manufacturing, & distributing high-quality APIs for the pharmaceutical industry innovatively & sustainably. Backed by a robust global network of 12 strategically located local offices, we cater to the needs of over 400 active customers in 70+ countries. At Suanfarma we offer our CDMO capacity for fermentation & chemical synthesis projects, offering a One Stop Shop service with a solid track record, & which allows us to achieve success in the development, scaling, manufacturing, & commercialization of an API, either innovative or generic.
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Lymecycline

About the Company : Shamrock Pharmachemi Pvt Ltd. is a globally recognized API leader with over 26 years of expertise in human and veterinary pharmaceuticals. Operating in 40+ countries, we own two st...

Shamrock Pharmachemi Pvt Ltd. is a globally recognized API leader with over 26 years of expertise in human and veterinary pharmaceuticals. Operating in 40+ countries, we own two state-of-the-art manufacturing facilities in Gujarat and collaborate with 16+ exclusive partner plants. Proudly holding the title of 'Largest Exporter for 12 Molecules Worldwide', we maintain the highest quality standards including USFDA, EU-GMP, WHO-GMP, and other stringent international certifications. Our robust regulatory compliance (DMF, CEP, ICH Q7) and customer-focused approach make us the preferred 'API Partner in India' for pharmaceutical companies worldwide
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Amara Labs

India
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About the Company : Amara Labs Pvt Ltd is a WHO-GMP certified manufacturing company wholly owned by a team of technocrats with working experience of more than 20 years in Multi-Nationals Companies lik...

Amara Labs Pvt Ltd is a WHO-GMP certified manufacturing company wholly owned by a team of technocrats with working experience of more than 20 years in Multi-Nationals Companies like Mylan and Cipla. We offer Active Pharmaceutical Ingredients, custom synthesis for Domestic, Intermediates for regulated markets with a key focus on new molecules. The manufacturing facility for production is equipped with an ability of producing Active Pharmaceutical Ingredients(API’s) in cGMP standards, with additional facilities of Pilot Plant with a full suite for scaling up and validation of new molecules
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About the Company : Calidrux Lifesciences LLP, established in 2023 in Gujarat, is a leading wholesaler of Active Pharmaceutical Ingredients (APIs), acid dyes, and more. Committed to quality and reliab...

Calidrux Lifesciences LLP, established in 2023 in Gujarat, is a leading wholesaler of Active Pharmaceutical Ingredients (APIs), acid dyes, and more. Committed to quality and reliability, we provide high-grade products to meet the diverse needs of the pharmaceutical and chemical industries. With a focus on excellence and customer satisfaction, we strive to deliver superior solutions that contribute to the growth and success of our clients, while ensuring compliance with industry standards.
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About the Company : Enaltec Labs was established in 2006 by a group of young & experienced professionals with the specific objective to develop & produce complex, small volume, technology driven produ...

Enaltec Labs was established in 2006 by a group of young & experienced professionals with the specific objective to develop & produce complex, small volume, technology driven products at competitive prices, thus providing the critical India advantage to generic formulators across the world. The paradigm shift of leading Indian pharmaceutical companies to target high volume and blockbuster products for regulated markets has been the inspiration behind the launch of Enaltec Labs.
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Kopran

India
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About the Company : Kopran is the group company of Parijat Enterprises. Kopran is currently an integrated Pharmaceutical Company manufacturing a large range of products. It manufactures both Active...

Kopran is the group company of Parijat Enterprises. Kopran is currently an integrated Pharmaceutical Company manufacturing a large range of products. It manufactures both Active Pharmaceutical Ingredients and Finished Dosage Forms. Kopran’s products are registered globally and its facilities match best of international standards and are approved by various Regulatory authorities. Kopran is focused on improvement in technology and new products duly integrated through their sophisticated Research & Development department.
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Olon S.p.A

Italy
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About the Company : We produce Active Pharmaceutical Ingredients (APIs) providing integrated full-service capabilities. Olon’s ability to develop and manufacture Active Pharmaceutical Ingredients (...

We produce Active Pharmaceutical Ingredients (APIs) providing integrated full-service capabilities. Olon’s ability to develop and manufacture Active Pharmaceutical Ingredients (APIs) in our network of facilities allows clients full access to integrated services resulting in faster production and delivery timelines, with one of the most extensive track records. We rely on synthetic and biological processes both for generic and contract development and the manufacturing market, in a full cGMPs environment, following ICH Q7 compliance.
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About the Company : Haorui, established in 1997, is a manufacturer and supplier of APIs, intermediates, veterinary and food additives. Meanwhile, it is assisting global pharmaceutical companies to get...

Haorui, established in 1997, is a manufacturer and supplier of APIs, intermediates, veterinary and food additives. Meanwhile, it is assisting global pharmaceutical companies to get the domestic registration of their finished dosage for their international expansion. Our USFDA approved products Flumazenil, Granisetron HCl, Granisetron Base, Docetaxel Anhydrous, Irinotecan HCl, Dasatinib Monohydrate, Oxaliplatin and Temozolomide have been recognized by our customers globally. In addition, our Amisulpride API acquired CEP, UK GMP & USDMF.
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11-Feb-2022
27-Mar-2025
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ABOUT THIS PAGE

Looking for 992-21-2 / Lymecycline API manufacturers, exporters & distributors?

Lymecycline manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Lymecycline 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 Lymecycline manufacturer or Lymecycline supplier for your needs.

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

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

API | Excipient name

Lymecycline

Synonyms

Tetralysal, N-lysinomethyltetracycline, Limeciclina, Lymecyclinum, Tetracycline-l-methylenelysine, Ciclolysal

Cas Number

992-21-2

Unique Ingredient Identifier (UNII)

7D6EM3S13P

About Lymecycline

A semisynthetic antibiotic related to TETRACYCLINE. It is more readily absorbed than TETRACYCLINE and can be used in lower doses.

Lymecycline Manufacturers

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

Lymecycline Suppliers

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

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

Lymecycline CEP

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

A Lymecycline CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Lymecycline 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 Lymecycline suppliers with CEP (COS) on PharmaCompass.

Lymecycline WC

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

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

Lymecycline GMP

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

Lymecycline CoA

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

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

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