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Chemistry

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Also known as: 820211-82-3, Elafin, Human elafin, Tiprelestat [inn], Trappin-2, Unii-78i8295690
Molecular Formula
C254H416N72O75S10
Molecular Weight
5999  g/mol
InChI Key
MDCUNMLZLNGCQA-HWOAGHQOSA-N

Tiprelestat
A secretory proteinase inhibitory protein that was initially purified from human SKIN. It is found in a variety mucosal secretions and is present at high levels in SPUTUM. Elafin may play a role in the innate immunity (IMMUNITY, INNATE) response of the LUNG.
1 2D Structure

Tiprelestat

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(1R,4S,4aS,7S,7aS,10S,10aS,13aR,16S,20aS,22S,23aS,25S,26aS,28S,29aS,31S,32aS,34R,37S,40S,43S,46S,49S,52S,58R,63R,66S,72S,75R,81S,84S,87R,92R,98S)-58-[[(2S)-2-[[2-[[(2S)-1-[(2S)-6-amino-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoyl]amino]-4-carboxybutanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-7a,10a,23a-tris(4-aminobutyl)-7,22-bis(2-amino-2-oxoethyl)-4a,40,46,49-tetrakis[(2S)-butan-2-yl]-4,37-bis(3-carbamimidamidopropyl)-66-(2-carboxyethyl)-26a,32a-bis(carboxymethyl)-29a-[(1R)-1-hydroxyethyl]-72-(hydroxymethyl)-31,84-dimethyl-20a,25,43-tris(2-methylpropyl)-28,81-bis(2-methylsulfanylethyl)-2a,3,5a,6,8a,9,11a,15,18a,21,21a,24,24a,27,27a,30,30a,33,33a,35a,36,39,42,45,48,51,57,64,67,70,73,76,79,82,85,93,99-heptatriacontaoxo-15a,16a,38a,39a,60,61,89,90-octathia-a,2,3a,5,6a,8,9a,12a,14,19a,20,22a,23,25a,26,28a,29,31a,32,34a,35,36a,38,41,44,47,50,56,65,68,71,74,77,80,83,86,94-heptatriacontazaoctacyclo[90.25.17.434,75.263,113.010,14.016,20.052,56.094,98]tetracontahectane-87-carbonyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-5-amino-5-oxopentanoic acid
2.1.2 InChI
InChI=1S/C254H416N72O75S10/c1-28-129(17)195-239(387)288-142(60-38-43-85-258)208(356)283-141(59-37-42-84-257)210(358)306-168-120-407-406-119-167-228(376)294-152(99-123(5)6)215(363)284-140(58-36-41-83-256)209(357)296-158(106-191(347)348)221(369)317-200(137(25)331)244(392)299-157(105-190(345)346)218(366)308-169(248(396)321-91-49-65-172(321)231(379)274-110-186(339)310-195)121-410-408-117-165(227(375)295-155(102-138-55-33-32-34-56-138)220(368)313-194(128(15)16)251(399)325-95-53-68-175(325)232(380)292-151(252(400)401)73-77-180(262)333)302-203(351)135(23)276-207(355)147(80-97-402-26)278-183(336)107-272-206(354)163-115-404-405-116-164(225(373)277-134(22)202(350)282-148(81-98-403-27)214(362)293-153(100-124(7)8)216(364)300-159(104-182(264)335)247(395)326-96-54-71-178(326)250(398)324-94-52-67-174(324)233(381)297-156(103-181(263)334)217(365)285-143(211(359)305-167)62-45-87-269-253(265)266)304-212(360)144(63-46-88-270-254(267)268)289-240(388)196(130(18)29-2)314-219(367)154(101-125(9)10)298-241(389)197(131(19)30-3)316-242(390)198(132(20)31-4)315-236(384)177-70-51-93-323(177)249(397)170(122-411-409-118-166(307-229(168)377)226(374)286-145(74-78-188(341)342)205(353)271-108-184(337)279-160(112-327)222(370)303-163)309-223(371)161(113-328)280-185(338)109-273-230(378)171-64-48-90-320(171)245(393)149(61-39-44-86-259)291-243(391)199(136(24)330)318-224(372)162(114-329)301-238(386)193(127(13)14)311-234(382)173-66-47-89-319(173)187(340)111-275-204(352)139(57-35-40-82-255)287-237(385)192(126(11)12)312-235(383)176-69-50-92-322(176)246(394)150(75-79-189(343)344)290-213(361)146(72-76-179(261)332)281-201(349)133(21)260/h32-34,55-56,123-137,139-178,192-200,327-331H,28-31,35-54,57-122,255-260H2,1-27H3,(H2,261,332)(H2,262,333)(H2,263,334)(H2,264,335)(H,271,353)(H,272,354)(H,273,378)(H,274,379)(H,275,352)(H,276,355)(H,277,373)(H,278,336)(H,279,337)(H,280,338)(H,281,349)(H,282,350)(H,283,356)(H,284,363)(H,285,365)(H,286,374)(H,287,385)(H,288,387)(H,289,388)(H,290,361)(H,291,391)(H,292,380)(H,293,362)(H,294,376)(H,295,375)(H,296,357)(H,297,381)(H,298,389)(H,299,392)(H,300,364)(H,301,386)(H,302,351)(H,303,370)(H,304,360)(H,305,359)(H,306,358)(H,307,377)(H,308,366)(H,309,371)(H,310,339)(H,311,382)(H,312,383)(H,313,368)(H,314,367)(H,315,384)(H,316,390)(H,317,369)(H,318,372)(H,341,342)(H,343,344)(H,345,346)(H,347,348)(H,400,401)(H4,265,266,269)(H4,267,268,270)/t129-,130-,131-,132-,133-,134-,135-,136+,137+,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,192-,193-,194-,195-,196-,197-,198-,199-,200-/m0/s1
2.1.3 InChI Key
MDCUNMLZLNGCQA-HWOAGHQOSA-N
2.1.4 Canonical SMILES
CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC2CSSCC3C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C4CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N5CCCC5C(=O)N6CCCC6C(=O)NC(C(=O)NC(C(=O)N3)CCCNC(=N)N)CC(=O)N)CC(=O)N)CC(C)C)CCSC)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C7CCCN7C(=O)C(CSSCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N4)CO)CCC(=O)O)NC2=O)NC(=O)C(CO)NC(=O)CNC(=O)C8CCCN8C(=O)C(CCCCN)NC(=O)C(C(C)O)NC(=O)C(CO)NC(=O)C(C(C)C)NC(=O)C9CCCN9C(=O)CNC(=O)C(CCCCN)NC(=O)C(C(C)C)NC(=O)C2CCCN2C(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(C)N)C(C)CC)C(C)CC)CC(C)C)C(C)CC)CCCNC(=N)N)CCSC)C)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(C(C)C)C(=O)N2CCCC2C(=O)NC(CCC(=O)N)C(=O)O)C(=O)N2CCCC2C(=O)NCC(=O)N1)CC(=O)O)C(C)O)CC(=O)O)CCCCN)CC(C)C)CCCCN)CCCCN
2.1.5 Isomeric SMILES
CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H]4CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N5CCC[C@H]5C(=O)N6CCC[C@H]6C(=O)N[C@H](C(=O)N[C@H](C(=O)N3)CCCNC(=N)N)CC(=O)N)CC(=O)N)CC(C)C)CCSC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]7CCCN7C(=O)[C@H](CSSC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N4)CO)CCC(=O)O)NC2=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@@H]8CCCN8C(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]9CCCN9C(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C)N)[C@@H](C)CC)[C@@H](C)CC)CC(C)C)[C@@H](C)CC)CCCNC(=N)N)CCSC)C)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](C(C)C)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CCC(=O)N)C(=O)O)C(=O)N2CCC[C@H]2C(=O)NCC(=O)N1)CC(=O)O)[C@@H](C)O)CC(=O)O)CCCCN)CC(C)C)CCCCN)CCCCN
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Antileukoproteinase, Skin-derived

2. Elafin

3. Inhibitor Wap3, Protease

4. Peptidase Inhibitor 3, Skin Derived

5. Peptidase Inhibitor 3, Skin-derived

6. Protease Inhibitor 3, Skin Derived

7. Protease Inhibitor 3, Skin-derived

8. Protease Inhibitor Wap3

9. Skin Derived Antileukoproteinase

10. Skin-derived Antileukoproteinase

2.2.2 Depositor-Supplied Synonyms

1. 820211-82-3

2. Elafin

3. Human Elafin

4. Tiprelestat [inn]

5. Trappin-2

6. Unii-78i8295690

7. Dtxsid00231519

8. Human Elafin (elastase-specific Inhibitor, Skin-derived Antileukoproteinase, Peptidase Inhibitor 3)

9. 78i8295690

2.3 Create Date
2009-09-22
3 Chemical and Physical Properties
Molecular Weight 5999 g/mol
Molecular Formula C254H416N72O75S10
XLogP3-25.6
Hydrogen Bond Donor Count74
Hydrogen Bond Acceptor Count93
Rotatable Bond Count115
Exact Mass5996.8225594 g/mol
Monoisotopic Mass5994.8158498 g/mol
Topological Polar Surface Area2550 Ų
Heavy Atom Count411
Formal Charge0
Complexity15200
Isotope Atom Count0
Defined Atom Stereocenter Count58
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

Investigated for use/treatment in inflammatory disorders (unspecified).


Treatment of oesophageal carcinoma


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Protease Inhibitors

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)


5.2 Mechanism of Action

Elafin is able to abrogate lipopolysaccharide-induced production of monocyte chemotactic protein 1 in monocytes by inhibiting AP-1 and NFkappaB activation. Due to its selective expression at mucosal surfaces as well as in alveolar macrophages, monocytes and neutrophils, the ability of Elafin to inhibit the lipopolysaccharide signaling pathway may be important in disease states such as cystic fibrosis, pneumonia, and acute respiratory distress syndrome. The inhibition of two key inflammatory pathways confirms the importance of Elafin as a mediator of the innate immune response.


ABOUT THIS PAGE

Tiprelestat Manufacturers

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

Tiprelestat Suppliers

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

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

Tiprelestat USDMF

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

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

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

Tiprelestat WC

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

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

Tiprelestat GMP

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

Tiprelestat CoA

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

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

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