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Chemistry

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Also known as: 157283-68-6, Travatan, Travatan z, Izba, Al-6221, Travaprost
Molecular Formula
C26H35F3O6
Molecular Weight
500.5  g/mol
InChI Key
MKPLKVHSHYCHOC-AHTXBMBWSA-N
FDA UNII
WJ68R08KX9

Travoprost
A cloprostenol derivative that is used as an ANTIHYPERTENSIVE AGENT in the treatment of OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.
Travoprost is a Prostaglandin Analog.
1 2D Structure

Travoprost

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate
2.1.2 InChI
InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1
2.1.3 InChI Key
MKPLKVHSHYCHOC-AHTXBMBWSA-N
2.1.4 Canonical SMILES
CC(C)OC(=O)CCCC=CCC1C(CC(C1C=CC(COC2=CC=CC(=C2)C(F)(F)F)O)O)O
2.1.5 Isomeric SMILES
CC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](COC2=CC=CC(=C2)C(F)(F)F)O)O)O
2.2 Other Identifiers
2.2.1 UNII
WJ68R08KX9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (((1r)-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic Acid, 1-methylethyl Ester

2. Al 6221

3. Al-6221

4. Al6221

5. Travatan

6. Travatan Z

7. Z, Travatan

2.3.2 Depositor-Supplied Synonyms

1. 157283-68-6

2. Travatan

3. Travatan Z

4. Izba

5. Al-6221

6. Travaprost

7. Trovoprost

8. Otx-tp

9. Chebi:746859

10. Propan-2-yl (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate

11. Al6221

12. Wj68r08kx9

13. Nsc-760366

14. Travoprost [usan]

15. Travatanz

16. (z)-isopropyl 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((r,e)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate

17. Isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-{(1e,3r)-3-hydroxy-4-[(alpha,alpha,alpha-trifluoro-m-tolyl)oxy]-1-butenyl}cyclopentyl)-5-heptenoate

18. Travatan (tn)

19. 5-heptenoic Acid, 7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-, 1-methylethyl Ester, (5z)-

20. Propan-2-yl (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate

21. Propan-2-yl (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-{(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl}cyclopentyl]hept-5-enoate

22. Travoprostum

23. Unii-wj68r08kx9

24. (((1r)-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic Acid, 1-methylethyl Ester

25. (+)-fluprostenol Isopropyl Ester

26. Travoprost [usan:usp:inn:ban]

27. Travoprost In Bulk

28. Travoprostintermediates

29. Travoprost [mi]

30. Travoprost [inn]

31. Travoprost [jan]

32. Travoprost [vandf]

33. Travoprost [mart.]

34. Travoprost [usp-rs]

35. Travoprost [who-dd]

36. Schembl93818

37. Travoprost (jan/usp/inn)

38. (1r-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic Acid, 1-methylethyl Ester

39. (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((1e,3r)-3-hydroxy-4-((alpha,alpha,alpha-trifluoro-m-isopropyl-tolyl)oxy)-1-butenyl)cyclopentyl)-5-heptenoate

40. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, 1-methylethyl Ester, (1r-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-

41. Travoprost [ema Epar]

42. Gtpl7102

43. Chembl1200799

44. Travoprost [orange Book]

45. Dtxsid80896948

46. Travoprost [usp Monograph]

47. Duotrav Component Travoprost

48. Ex-a1772

49. Hy-b0584

50. Zinc4474682

51. Bdbm50248302

52. S3738

53. Akos024458039

54. Travoprost Component Of Duotrav

55. Ac-6103

56. Am84515

57. Ccg-269692

58. Db00287

59. Nsc 760366

60. Ncgc00346741-02

61. 5-heptenoic Acid, 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((1e,3r)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, 1-methylethyl Ester, (5z)-

62. Bs-15509

63. Fluprostenol Isopropyl Ester;al6221;flu-ipr

64. D01964

65. 283t686

66. Sr-01000942266

67. Sr-01000946860

68. J-502633

69. Q2193376

70. Sr-01000942266-1

71. Sr-01000946860-1

72. Fluprostenol Isopropyl Ester, >=98%, Ethanol Solution

73. (1r-(1.alpha.(z),2.beta.(1e,3r*),3.alpha.,5.alpha.))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic Acid, 1-methylethyl Ester

74. (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-5-heptenoic Acid 1-methyethyl Ester

75. (z)-isopropyl 7-((1r,2r)-3,5-dihydroxy-2-((s,e)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate

76. (z)-isopropyl 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((r,e)-3-hydroxy-4-(3-(trifluoromethyl) Phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate

77. (z)-isopropyl7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((r,e)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate

78. Isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((1e,3r)-3-hydroxy-4-((.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy)-1-butenyl)cyclopentyl)-5-heptenoate

79. Isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((3r,e)-3-hydroxy-4-(3-(trifluoromethyl)-phenoxy)-but-1-enyl)-cyclopentyl)-hept-5-enoate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 500.5 g/mol
Molecular Formula C26H35F3O6
XLogP34.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count13
Exact Mass500.23857332 g/mol
Monoisotopic Mass500.23857332 g/mol
Topological Polar Surface Area96.2 Ų
Heavy Atom Count35
Formal Charge0
Complexity693
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameTravatan z
PubMed HealthTravoprost (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTravoprost is a synthetic prostaglandin F analogue. Its chemical name is [1R-[1(Z),2(1E,3R*),3,5]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid, 1-methylethylester. It has a molecular f...
Active IngredientTravoprost
Dosage FormSolution/drops
RouteOphthalmic
Strength0.004%
Market StatusPrescription
CompanyAlcon Pharms

2 of 4  
Drug NameTravoprost
PubMed HealthTravoprost (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTravoprost is a synthetic prostaglandin F analogue. Its chemical name is [1R-[1(Z),2(1E,3R*),3,5]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid, 1-methylethylester. It has a molecular f...
Active IngredientTravoprost
Dosage FormSolution/drops; Solution
RouteOphthalmic; ophthalmic
Strength0.004%
Market StatusTentative Approval; Prescription
CompanyPar Pharm

3 of 4  
Drug NameTravatan z
PubMed HealthTravoprost (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTravoprost is a synthetic prostaglandin F analogue. Its chemical name is [1R-[1(Z),2(1E,3R*),3,5]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid, 1-methylethylester. It has a molecular f...
Active IngredientTravoprost
Dosage FormSolution/drops
RouteOphthalmic
Strength0.004%
Market StatusPrescription
CompanyAlcon Pharms

4 of 4  
Drug NameTravoprost
PubMed HealthTravoprost (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTravoprost is a synthetic prostaglandin F analogue. Its chemical name is [1R-[1(Z),2(1E,3R*),3,5]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid, 1-methylethylester. It has a molecular f...
Active IngredientTravoprost
Dosage FormSolution/drops; Solution
RouteOphthalmic; ophthalmic
Strength0.004%
Market StatusTentative Approval; Prescription
CompanyPar Pharm

4.2 Drug Indication

Travoprost ophthalmic solution is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Travoprost is also currently indicated for the decrease of elevated intraocular pressure in paediatric patients aged 2 months to < 18 years with ocular hypertension or paediatric glaucoma.


FDA Label


Decrease of elevated intraocular pressure in adult patients with ocular hypertension or open-angle glaucoma (see section 5. 1). Decrease of elevated intraocular pressure in paediatric patients aged 3 years to < 18 years with ocular hypertension or paediatric glaucoma.


Decrease of elevated intraocular pressure in adult patients with ocular hypertension or open-angle glaucoma (see section 5. 1).

Decrease of elevated intraocular pressure in paediatric patients aged 2 months to < 18 years with ocular hypertension or paediatric glaucoma (see section 5. 1).


Treatment of glaucoma


5 Pharmacology and Biochemistry
5.1 Pharmacology

Travoprost, an isopropyl ester prodrug, is a synthetic prostaglandin F2 alpha analog that is rapidly hydrolyzed by esterases in the cornea to its biologically active free acid. The travoprost free acid is potent and highly selective for the FP prostanoid receptor.


5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TRAVOPROST
5.3.2 FDA UNII
WJ68R08KX9
5.3.3 Pharmacological Classes
Prostaglandins [CS]; Prostaglandin Analog [EPC]
5.4 ATC Code

S01EE04


S01EE04


S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01EE - Prostaglandin analogues

S01EE04 - Travoprost


5.5 Absorption, Distribution and Excretion

Absorption

Travoprost is systemically absorbed through the cornea. In humans, peak plasma concentrations of travoprost free acid were low (25 pg/mL or less) and occurred within 30 minutes following topical ocular administration of one drop of 0.004% travoprost ophthalmic solution.


Route of Elimination

Less than 2% of the topical ocular dose of travoprost was excreted in the urine within 4 hours as the travoprost free acid. Moreover, elimination from plasma is rapid, resulting in concentrations below the limit of quantitation (< 10 pg/mL) by one hour. Furthermore, in rats, 95% of a subcutaneous radiolabeled dose was eliminated within 24 hours. The major route of elimination was via the bile (61%) with the remainder excreted by the kidneys.


Volume of Distribution

Given the data currently available, it has been recorded that travoprost free acid is moderately distributed into body tissues with a volume of distribution of 2.6 L/kg in rats.


Clearance

Data regarding the clearance of travoprost is not readily available or accessible.


5.6 Metabolism/Metabolites

Travoprost, an isopropyl ester prodrug, is hydrolyzed by esterases in the cornea to its biologically active free acid. Systemically, travoprost free acid is rapidly and extensively metabolized in the kidney, liver, and lung to inactive metabolites via beta-oxidation of the α(carboxylic acid) chain to give the 1,2-dinor and 1,2,3,4-tetranor analogs, via oxidation of the 15-hydroxyl moiety, as well as via reduction of the 13,14 double bond.


5.7 Biological Half-Life

The terminal elimination half-life of travoprost free acid is determined to be approximately 45 minutes, although studies demonstrated half-life values that ranged from 17 to 86 minutes.


5.8 Mechanism of Action

Travoprost, a prostaglandin F2 analogue, is a highly selective full agonist which has a high affinity for the prostaglandin FP receptor, and facilitates reductions in intraocular pressure by increasing the outflow of aqueous humour via trabecular meshwork and uveoscleral pathways. Reduction of the intraocular pressure in man starts about 2 hours after administration and maximum effect is reached after 12 hours. Significant lowering of intraocular pressure can be maintained for periods exceeding 24 hours with a single dose.


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11-Apr-2022
28-Feb-2025
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ABOUT THIS PAGE

Looking for 157283-68-6 / Travoprost API manufacturers, exporters & distributors?

Travoprost manufacturers, exporters & distributors 1

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

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

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

API | Excipient name

Travoprost

Synonyms

157283-68-6, Travatan, Travatan z, Izba, Al-6221, Travaprost

Cas Number

157283-68-6

Unique Ingredient Identifier (UNII)

WJ68R08KX9

About Travoprost

A cloprostenol derivative that is used as an ANTIHYPERTENSIVE AGENT in the treatment of OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.

Travatan Z Manufacturers

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

Travatan Z Suppliers

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

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

Travatan Z USDMF

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

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

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

Travatan Z JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Travatan Z Drug Master File in Japan (Travatan Z JDMF) empowers Travatan Z API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Travatan Z JDMF during the approval evaluation for pharmaceutical products. At the time of Travatan Z JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Travatan Z suppliers with JDMF on PharmaCompass.

Travatan Z KDMF

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

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

After submitting a Travatan Z 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 Travatan Z API can apply through the Korea Drug Master File (KDMF).

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

Travatan Z WC

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

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

Travatan Z GMP

Travatan Z 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 Travatan Z 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 Travatan Z GMP manufacturer or Travatan Z GMP API supplier for your needs.

Travatan Z CoA

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

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

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