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Teprotide
Names
	IUPAC name 5-oxo-L-prolyl-L-tryptophyl-L-prolyl-N5-(diaminomethylidene)-L-ornithyl-L-prolyl-L-glutaminyl-L-isoleucyl-L-prolyl-L-proline
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	391608;
PubChem CID	443376;
	InChI InChI=1S/C53H76N14O12/c1-3-29(2)43(51(77)66-25-9-16-39(66)50(76)67-26-10-17-40(67)52(78)79)63-45(71)34(18-20-41(54)68)60-46(72)37-14-7-23-64(37)48(74)35(13-6-22-57-53(55)56)61-47(73)38-15-8-24-65(38)49(75)36(62-44(70)33-19-21-42(69)59-33)27-30-28-58-32-12-5-4-11-31(30)32/h4-5,11-12,28-29,33-40,43,58H,3,6-10,13-27H2,1-2H3,(H2,54,68)(H,59,69)(H,60,72)(H,61,73)(H,62,70)(H,63,71)(H,78,79)(H4,55,56,57)/t29-,33-,34-,35-,36-,37-,38-,39-,40-,43-/m0/s1;
	SMILES O=C(O)[C@H]7N(C(=O)[C@H]6N(C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]5N(C(=O)[C@@H](NC(=O)[C@H]4N(C(=O)[C@@H](NC(=O)[C@H]1NC(=O)CC1)Cc3c2ccccc2nc3)CCC4)CCC/N=C(\N)N)CCC5)CCC(=O)N)[C@@H](C)CC)CCC6)CCC7;
Properties
Chemical formula	C53H76N14O12
Molar mass	1101.257
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tracking categories (test):

SizeSet

Teprotide is nonapeptide which has been isolated from the snake ''Bothrops jararaca''. It is an angiotensin converting enzyme (ACE) inhibitor, which inhibits the conversion of angiotensin I to angiotensin II and may potentiate some of the pharmacological actions of bradykinin. It has a molecular formula of C₅₃H₇₆N₁₄O₁₂ and has been looked at as an antihypertension agent.

Isolation and Synthesis[edit]

The antihypertensive effects of teprotide were first observed by Sergio Ferreira in 1965 ^[1] and it was first isolated by Ferreira et al^[2] along with eight other peptides in 1970. Teprotide was synthesized in 1970 by Ondetti et al.^[3] and from there its antihypertensive properties were studied more closely.

Medical Use[edit]

Teprotide was chosen as a lead because of its long-lasting in vivo activity. This was demonstrated by Bianchi et. al.^[4] by administering teprotide to dogs and rats and observing that it inhibited the vasopressor response induced by angiotensin I.  Teprotide was shown to be an effective antihyperension agent but it had limited use because of its expense and lack of oral activity.  It was found that teprotide inhibits the enzyme that converts angiotensin I to angiotensin II.  From this researchers conducted structure-activity studies which allowed them to identify the active binding site of the ACE which allowed for the development of antihypertension drugs to be developed. Captopril was the first antihypertension drug developed by Ondetti and Cushman^[5] .

References[edit]

^ Ferreira, Sergio (1965). "A bradykinin-potentiating factor (bpf) present in the venom of bothrops jararaca". British Journal of Pharmacology. 24: 169–169. PMID PMC1704050. {{cite journal}}: Check |pmid= value (help); Unknown parameter |month= ignored (help)
^ Ferreira, Sergio H. (1970). "Isolation of bradykinin-potentiating peptides from Bothrops jararaca venom". Biochemistry. 9 (13): 2583–2593. doi:10.1021/bi00815a005. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
^ Ondetti, Miguel A. (1971). "Angiotensin-converting enzyme inhibitors from the venom of bothrops jararaca. Isolation, elucidation of structure, and synthesis". Biochemistry. 19 (22): 4033–4039. doi:10.1021/bi00798a004. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
^ Bianchi, A. (1973). "Inhibittion by SQ 20881 of vasopressor response to angiotensin I in conscious animals". European Journal of Pharmocology. 23 (2): 90–96. doi:10.1016/0014-2999(73)90248-3. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
^ Cushman, D.W. (1991). "History of the design of captopril and related inhibitors of angiotensin converting enzyme". Hypertension. 17 (4): 589–592. PMID 2013486. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

Category:Peptides

[1] Ferreira, Sergio (1965). "A bradykinin-potentiating factor (bpf) present in the venom of bothrops jararaca". British Journal of Pharmacology. 24: 169–169. PMID PMC1704050. {{cite journal}}: Check |pmid= value (help); Unknown parameter |month= ignored (help)

[2] Ferreira, Sergio H. (1970). "Isolation of bradykinin-potentiating peptides from Bothrops jararaca venom". Biochemistry. 9 (13): 2583–2593. doi:10.1021/bi00815a005. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

[3] Ondetti, Miguel A. (1971). "Angiotensin-converting enzyme inhibitors from the venom of bothrops jararaca. Isolation, elucidation of structure, and synthesis". Biochemistry. 19 (22): 4033–4039. doi:10.1021/bi00798a004. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

[4] Bianchi, A. (1973). "Inhibittion by SQ 20881 of vasopressor response to angiotensin I in conscious animals". European Journal of Pharmocology. 23 (2): 90–96. doi:10.1016/0014-2999(73)90248-3. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

[5] Cushman, D.W. (1991). "History of the design of captopril and related inhibitors of angiotensin converting enzyme". Hypertension. 17 (4): 589–592. PMID 2013486. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

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