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    Also known as: 147221-93-0, Delavirdine (mesylate), Rescriptor, Delavirdine mesilate, U-90152s, Delavirdine methanesulfonate
    Molecular Formula
    C23H32N6O6S2
    Molecular Weight
    552.7  g/mol
    InChI Key
    MEPNHSOMXMALDZ-UHFFFAOYSA-N
    FDA UNII
    421105KRQE
    Delavirdine
    A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1.
    1 2D Structure

    Delavirdine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methanesulfonic acid;N-[2-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazine-1-carbonyl]-1H-indol-5-yl]methanesulfonamide
    2.1.2 InChI
    InChI=1S/C22H28N6O3S.CH4O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20;1-5(2,3)4/h4-8,13-15,24-26H,9-12H2,1-3H3;1H3,(H,2,3,4)
    2.1.3 InChI Key
    MEPNHSOMXMALDZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)NS(=O)(=O)C.CS(=O)(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    421105KRQE
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Delavirdine

    2. Mesylate, Delavirdine

    3. Rescriptor

    4. U 90152

    5. U 90152s

    6. U-90152

    7. U-90152s

    8. U90152

    9. U90152s

    2.3.2 Depositor-Supplied Synonyms

    1. 147221-93-0

    2. Delavirdine (mesylate)

    3. Rescriptor

    4. Delavirdine Mesilate

    5. U-90152s

    6. Delavirdine Methanesulfonate

    7. Delavirdine Mesylate [usan]

    8. Delavirdine Monomethanesulfonate

    9. N-(2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1h-indol-5-yl)methanesulfonamide Methanesulfonate

    10. Chebi:4379

    11. 1-(3-(isopropylamino)-2-pyridyl)-4-((5-methanesulfonamidoindol-2-yl)carbonyl)piperazine Monomethanesulfonate

    12. 421105krqe

    13. Methanesulfonamide, N-[2-[[4-[3-[(1-methylethyl)amino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1h-indol-5-yl]-, Methanesulfonate (1:1)

    14. Delavirdine Mesilate (jan)

    15. Delavirdine Mesylate (usan)

    16. U 90152 (mesylate);bhap-u 90152 (mesylate)

    17. Delavirdine Mesilate [jan]

    18. Piperazine, 1-(3-((1-methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulfonyl)amino)-1h-indol-2-yl)carbonyl)-, Monomethanesulfonate

    19. Unii-421105krqe

    20. Sr-05000001471

    21. Hsdb 7162

    22. Rescriptor (tn)

    23. Drg-0166

    24. U 90152e

    25. U 90152s

    26. U 90152t

    27. Chembl929

    28. U 90152 (mesylate)

    29. Schembl40522

    30. Bhap-u 90152 (mesylate)

    31. Dtxsid701017136

    32. Delavirdine Mesylate [hsdb]

    33. Bcp09460

    34. Delavirdine Mesylate [vandf]

    35. Delavirdine Mesilate [mart.]

    36. Hy-10571a

    37. S6452

    38. Delavirdine Mesylate [who-dd]

    39. Akos024458004

    40. At12830

    41. Cs-1661

    42. Delavirdine Mesylate, >=98% (hplc)

    43. Delavirdine Methanesulfonate [mi]

    44. Bs-15144

    45. Delavirdine Mesylate [orange Book]

    46. U-90152t

    47. Ft-0603116

    48. C08087

    49. D00895

    50. J-008332

    51. Sr-05000001471-2

    52. Q27068164

    53. 1-(3-(isopropylamino)-2-pyridyl)-4-((5-methanesulphonamidoindol-2-yl)carbonyl)piperazine Monomethanesulphonate

    54. 1-[3-[(1-methylethyl)amino]-2-pyridinyl]-4-[[5-[(methylsulfonyl)amino]-1h-indol-2-yl]carbonyl]-piperazine Monomethanesulfonate

    55. Methanesulfonic Acid;n-[2-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazine-1-carbonyl]-1h-indol-5-yl]methanesulfonamide

    56. N-(2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1h-indol-5-yl)methanesulfonamidemethanesulfonate

    57. N-[2-({4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl}carbonyl)-1h-indol-5-yl]methanesulfonamide Methanesulfonate

    58. N-{2-[4-(3-isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1h-indol-5-yl}-methanesulfonamide; Compound With Methanesulfonic Acid

    59. Piperazine, 1-(3-((1-methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulphonyl)amino)-1h-indol-2-yl)carbonyl)-, Monomethanesulphonate

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 552.7 g/mol
    Molecular Formula C23H32N6O6S2
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count6
    Exact Mass552.18247511 g/mol
    Monoisotopic Mass552.18247511 g/mol
    Topological Polar Surface Area182 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity842
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameRescriptor
    PubMed HealthDelavirdine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelRESCRIPTOR Tablets contain delavirdine mesylate, a synthetic non-nucleoside reverse transcriptase inhibitor of the human immunodeficiency virus type 1 (HIV-1). The chemical name of delavirdine mesylate is piperazine, 1-[3-[(1-methyl-ethyl)amino]-2-py...
    Active IngredientDelavirdine mesylate
    Dosage FormTablet
    RouteOral
    Strength200mg; 100mg
    Market StatusPrescription
    CompanyViiv Hlthcare

    2 of 2  
    Drug NameRescriptor
    PubMed HealthDelavirdine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelRESCRIPTOR Tablets contain delavirdine mesylate, a synthetic non-nucleoside reverse transcriptase inhibitor of the human immunodeficiency virus type 1 (HIV-1). The chemical name of delavirdine mesylate is piperazine, 1-[3-[(1-methyl-ethyl)amino]-2-py...
    Active IngredientDelavirdine mesylate
    Dosage FormTablet
    RouteOral
    Strength200mg; 100mg
    Market StatusPrescription
    CompanyViiv Hlthcare

    4.2 Therapeutic Uses

    Delavirdine is indicated in the treatment of HIV-1 infection in combination with other appropriate antiretroviral therapy. /Included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1042

    4.3 Drug Warning

    Plasma lipid and lipoprotein levels were measured at baseline and after 8 weeks of highly active antiretroviral therapy among patients receiving delavirdine with or without a protease inhibitor (PI). In patients receiving nucleoside reverse transcriptase inhibitors (NRTI) plus delavirdine, there was a statistically significant increase in cholesterol and HDL levels, whereas those receiving NRTI plus a PI had no significant change in their HDL levels. When delavirdine was combined with a PI, there was a more dramatic increase in both cholesterol and HDL concentrations.

    PMID:12218397 Roberts AD et al; AIDS 16 (13): 1829-30 (2002)

    Rash is the most frequently reported adverse effect of delavirdine. In 2 clinical studies..., rash was reported in 32-35% of adults who received the usual dosage of delavirdine in conjunction with nucleoside reverse transcriptase inhibitors compared with 16-21% of adults who received the nucleoside reverse transcriptase inhibitors alone. In these studies, grade 1 rash (erythema, pruritus), grade 2 rash (diffuse maculopapular rash, dry desquamation), or grade 3 rash (vesiculation, moist desquamation, ulceration) occurred in about 17, 14, and 4%, respectively, of patients receiving delavirdine in conjunction with nucleoside reverse transcriptase inhibitors compared with 12, 6, and 0%, respectively, of patients receiving the nucleoside reverse transcriptase inhibitors alone.There were no cases of grade 4 rash (erythema multiforme, Stevens-Johnson syndrome, toxic epidermal necrolysis, necrosis requiring surgery, exfoliative dermatitis) in either patient group. About 3-4% of patients receiving delavirdine in conjunction with nucleoside reverse transcriptase inhibitors discontinued treatment because of rash compared with 0-1% of patients who received the nucleoside reverse transcriptase inhibitors alone.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 633

    Delavirdine-associated rash occurs mainly on the upper body and proximal arms with decreasing intensity of the lesions on the neck and face and progressively less on the rest of the trunk and limbs. Rash usually is evident within the first few weeks following initiation of delavirdine therapy; occurrence of rash after 1 month of therapy is uncommon. Because there is no evidence that the incidence of rash is decreased by initiating delavirdine therapy using a low dose and then titrating dosage, dosage titration is not recommended.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 633

    Severe and life-threatening skin reactions, including Stevens-Johnson syndrome and erythema multiforme, have been reported rarely in patients receiving delavirdine; 2 cases of Stevens-Johnson syndrome were reported during postmarketing surveillance. These severe reactions resolved after the drug was discontinued..

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 633

    For more Drug Warnings (Complete) data for DELAVIRDINE MESYLATE (26 total), please visit the HSDB record page.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-HIV Agents

    Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

    Reverse Transcriptase Inhibitors

    Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

    5.2 Absorption, Distribution and Excretion

    Elimination: Fecal: 44% following multiple doses of 330 mg three times a day in healthy volunteers. Renal: 51%, following multiple doses of 330 mg three times a day in healthy volunteers. Less than 5% of the dose is recovered unchanged in urine.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1043

    Delavirdine is distributed predominantly into blood plasma.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1042

    Delavirdine is well absorbed, especially at pH less than 2.0.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1362

    Delavirdine mesylate is rapidly absorbed following oral administration, and peak plasma concentrations of the drug are attained approximately 1 hour after the dose. Following oral administration of 400 mg of delavirdine mesylate 3 times daily in HIV-infected adults, mean steady-state peak plasma concentrations of the drug are 15.98 ug/ml (range: 0.91-45.66 ug/ml), mean trough plasma concentrations are 6.85 ug/ml (range: 0.05-20.55 ug/ml), and mean AUC is 82.19 ughour/ml.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 638

    For more Absorption, Distribution and Excretion (Complete) data for DELAVIRDINE MESYLATE (8 total), please visit the HSDB record page.

    5.3 Metabolism/Metabolites

    Delavirdine binds extensively to plasma proteins and primarily is metabolized by CYP3A4. The major metabolic pathway results in N-dealkylation. There is considerable intersubject variability in plasma delavirdine concentrations related to differences in CYP3A activity. The CSF-to-plasma ratio is 0.02.

    Rom, W.N. (ed.). Environmental and Occupational Medicine. 2nd ed. Boston, MA: Little, Brown and Company, 1992., p. 1362

    The metabolism of delavirdine in the mouse was extensive and involved amide bond cleavage, N-desalkylation, hydroxylation at the C-6' position of the pyridine ring, and pyridine ring-cleavage as determined by MS and/or 1H and 13C NMR spectroscopies. N-desalkylation and amide bond cleavage were the primary metabolic pathways at low drug doses and, as the biotransformation of delavirdine to desalkyl delavirdine reached saturation or inhibition, amide bond cleavage became the predominant pathway at higher doses and after multiple doses.

    PMID:9224777 Chang M et al; Drug Metab Dispos 25 (7): 828-39 (1997)

    5.4 Biological Half-Life

    The apparent plasma half-life of delavirdine increases with dose. The mean plasma half-life of delavirdine is 5.8 hours (range: 2-11 hours) in adults receiving a dosage of 400 mg 3 times daily.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 638

    Elimination from plasma: Mean, 5.8 hours (range, 2 to 11 hours) following treatment with 400 mg three times a day. The apparent half-life increases with dose.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1042

    5.5 Mechanism of Action

    After entering the cell, delavirdine binds to a hydrophobic pocket in the p66 subunit of reverse transcriptase. This causes a conformational change to a stable, inactive form of the enzyme. The delavirdine-reverse transcriptase complex is stabilized by hydrogen bonds at residue Lys-103 and strong hydrophobic interactions with residue Pro-236. Much higher concentrations of delavirdine are required to inhibit cellular polymerase than reverse transcriptase.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1362

    While the complete mechanism of antiviral activity of delavirdine has not been fully elucidated, the drug inhibits replication of human immunodeficiency virus type 1 (HIV-1) by interfering with viral RNA- and DNA-directed polymerase activities of reverse transcriptase. HIV reverse transcriptase is essential for viral replication, and its activities occur in the host cell cytoplasm after the viral particle penetrates the cell membrane and releases the viral core, but before nuclear entry and chromosomal integration of proviral DNA. The enzyme is multifunctional, with 3 principal activities (ie., RNA-directed DNA polymerase, RNase H, and DNA-directed DNA polymerase functions). Using viral RNA as a template, reverse transcriptase forms a minus strand of viral DNA, creating a double-stranded RNA:DNA hybrid (i.e., RNA-directed DNA polymerase function). The RNase H function of reverse transcriptase facilitates copying of viral RNA by degrading the RNA component of the RNA:DNA hybrid after the RNA is copied, leaving a single minus strand of viral DNA. Using the newly formed minus strand of viral DNA as a template, reverse transcriptase forms the plus strand of viral DNA, converting single-stranded viral DNA to the double-stranded proviral DNA form (i.e, DNA-directed DNA polymerase function). BHAP derivatives, including delavirdine, inhibit the polymerase functions, but not the RNase H function, of reverse transcriptase. The drugs bind directly to heterodimeric HIV-1 reverse transcriptase and exert a virustatic effect by acting as a specific, noncompetitive HIV-1 reverse transcriptase inhibitor.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 637

    Nonnucleoside reverse transcriptase inhibitors affect reverse transcriptase at a different site than nucleoside reverse transcriptase inhibitors (e.g., abacavir, didanosine, lamivudine, stavudine, zalcitabine, zidovudine), and the drugs have different mechanisms of action. Unlike currently available nonnucleoside reverse transcriptase inhibitors, dideoxynucleoside antiretroviral agents require intracellular conversion to triphosphate metabolites, which then compete with naturally occurring deoxynucleoside triphosphates for incorporation into viral DNA by reverse transcriptase and cause premature viral DNA chain termination by preventing further 5 to 3 phosphodiester linkages.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 637

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    DOSAGE - TABLET;ORAL - 100MG

    USFDA APPLICATION NUMBER - 20705

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    DOSAGE - TABLET;ORAL - 200MG

    USFDA APPLICATION NUMBER - 20705

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    ABOUT THIS PAGE

    Looking for 147221-93-0 / Delavirdine API manufacturers, exporters & distributors?

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

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

    API | Excipient name

    Delavirdine

    Synonyms

    147221-93-0, Delavirdine (mesylate), Rescriptor, Delavirdine mesilate, U-90152s, Delavirdine methanesulfonate

    Cas Number

    147221-93-0

    Unique Ingredient Identifier (UNII)

    421105KRQE

    About Delavirdine

    A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1.

    DELAVIRDINE MESYLATE Manufacturers

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

    DELAVIRDINE MESYLATE Suppliers

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

    DELAVIRDINE MESYLATE GMP

    DELAVIRDINE MESYLATE 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 DELAVIRDINE MESYLATE 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 DELAVIRDINE MESYLATE GMP manufacturer or DELAVIRDINE MESYLATE GMP API supplier for your needs.

    DELAVIRDINE MESYLATE CoA

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

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

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