Tetracosactide (also known as Cosyntropin) is a synthetic peptide that is identical to the 24-amino acid segment (sequence: SYSMEHFRWGKPVGKKRRPVKVYP) at the N-terminal of adrenocorticotropic hormone. ACTH (1-24), a segment similar in all species, contains the biological activity that stimulates production of corticosteroids in the adrenal cortex. Tetracosactide exhibits the same activity as natural ACTH with regard to all its biological activities. The complex results in a product whose absorption in man is effected over a longer period of time as compared to corticotropin. Therefore, therapy may be maintained with less frequent administration.

Structure

Similar Structures

Synonyms

adrenocorticotropic hormone 1-24
Adrenocorticotropic hormone fragment 1-24 human, rat
alpha(1-24)-corticotrophin
ATCH (1-24)
beta(1-24)-corticotrophin
Corticotropin tetracosapeptide
corticotropin-(1-24)
corticotropin-(1-24) tetracosapeptide
Cosyntropin
Tetracosactida
Tetracosactide
Tetracosactrin
α1-24-corticotrophin
β1-24-corticotrophin

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Tetracosactide acetate	H86HJ92K8Y	22633-88-1	DFABUZLKSKOWCS-WMPFGLIOSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Cortrosyn	Injection, powder, lyophilized, for solution	0.25 mg/1mL	Intramuscular; Intravenous; Parenteral	General Injectables & Vaccines, Inc	2010-03-01	Not applicable
Cortrosyn	Injection, powder, lyophilized, for solution	0.25 mg/1mL	Intramuscular; Intravenous	Amphastar Pharmaceuticals, Inc.	2003-08-01	Not applicable
Cortrosyn Inj 0.25mg	Powder, for solution	0.25 mg	Intramuscular; Intravenous	Amphastar Pharmaceuticals, Inc.	1974-12-31	Not applicable
Cosyntropin	Injection, solution	0.25 mg/1mL	Intravenous	Sandoz	2008-02-21	2011-12-31
Synacthen Depot	Suspension	1 mg	Intramuscular	Mallinckrodt Specialty Pharmaceuticals Ireland Ltd.	1973-12-31	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Cosyntropin	Injection, powder, lyophilized, for solution	0.25 mg/1mL	Intramuscular; Intravenous	GeneraMedix	2009-12-18	2013-02-08
Cosyntropin	Injection, powder, lyophilized, for solution	0.25 mg/1mL	Intravenous	Sandoz	2012-06-29	Not applicable
Cosyntropin	Injection, powder, for solution	0.25 mg/1mL	Intramuscular; Intravenous	Mylan Institutional LLC	2013-04-24	Not applicable
Cosyntropin	Injection, powder, for solution	0.25 mg/1mL	Intramuscular; Intravenous	Mylan Institutional LLC	2012-07-27	2012-07-27

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

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Categories

UNII

72YY86EA29

CAS number

16960-16-0

Weight

Average: 2933.49
Monoisotopic: 2931.580641316

Chemical Formula

C₁₃₆H₂₁₀N₄₀O₃₁S

InChI Key

ZOEFCCMDUURGSE-SQKVDDBVSA-N

InChI

InChI=1S/C136H210N40O31S/c1-75(2)109(127(200)154-71-106(181)156-88(31-13-17-52-137)114(187)158-89(32-14-18-53-138)115(188)159-91(35-21-56-149-134(142)143)116(189)164-96(37-23-58-151-136(146)147)131(204)175-60-25-39-104(175)126(199)173-111(77(5)6)128(201)163-90(33-15-19-54-139)120(193)171-110(76(3)4)129(202)169-101(65-80-43-47-84(180)48-44-80)132(205)176-61-26-40-105(176)133(206)207)172-125(198)103-38-24-59-174(103)130(203)95(34-16-20-55-140)157-107(182)70-153-113(186)99(66-81-68-152-87-30-12-11-29-85(81)87)167-117(190)92(36-22-57-150-135(144)145)160-121(194)98(63-78-27-9-8-10-28-78)166-123(196)100(67-82-69-148-74-155-82)168-118(191)93(49-50-108(183)184)161-119(192)94(51-62-208-7)162-124(197)102(73-178)170-122(195)97(165-112(185)86(141)72-177)64-79-41-45-83(179)46-42-79/h8-12,27-30,41-48,68-69,74-77,86,88-105,109-111,152,177-180H,13-26,31-40,49-67,70-73,137-141H2,1-7H3,(H,148,155)(H,153,186)(H,154,200)(H,156,181)(H,157,182)(H,158,187)(H,159,188)(H,160,194)(H,161,192)(H,162,197)(H,163,201)(H,164,189)(H,165,185)(H,166,196)(H,167,190)(H,168,191)(H,169,202)(H,170,195)(H,171,193)(H,172,198)(H,173,199)(H,183,184)(H,206,207)(H4,142,143,149)(H4,144,145,150)(H4,146,147,151)/t86-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,109-,110-,111-/m0/s1

IUPAC Name

(2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-{2-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido]-4-(methylsulfanyl)butanamido]-4-carboxybutanamido]-3-(1H-imidazol-5-yl)propanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanamido]acetamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]acetamido}hexanamido]hexanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]hexanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxylic acid

SMILES

CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1CCC[C@H]1C(O)=O

Pharmacology

Indication

For use as a diagnostic agent in the screening of patients presumed to have adrenocortical insufficiency.

Associated Conditions

Pharmacodynamics

Cosyntropin exhibits the full corticosteroidogenic activity of natural ACTH. Various studies have shown that the biologic activity of ACTH resides in the N- terminal portion of the molecule and that the 1-20 amino acid residue is the minimal sequence retaining full activity. Partial or complete loss of activity is noted with progressive shortening of the chain beyond 20 amino acid residue. For example, the decrement from 20 to 19 results in a 70% loss of potency. The pharmacologic profile of Cosyntropin is similar to that of purified natural ACTH. It has been established that 0.25 mg of Cosyntropin will stimulate the adrenal cortex maximally and to the same extent as 25 units of natural ACTH. Cosyntropin has less immunogenic activity than ACTH because the amino acid sequence having most of the antigenic activity of ACTH, i.e., amino acids 25-39, is not present in cosyntropin. The extra-adrenal effects which natural ACTH and Cosyntropin have in common include increased melanotropic activity, increased growth hormone secretion and an adipokinetic effect. These are considered to be without physiological or clinical significance.

Mechanism of action

Cosyntropin combines with a specific receptor in the adrenal cell plasma membrane and, in patients with normal adrenocortical function, stimulates the initial reaction involved in the synthesis of adrenal steroids (including cortisol, cortisone, weak androgenic substances, and a limited quantity of aldosterone) from cholesterol by increasing the quantity of the substrate within the mitochondria. Cosyntropin does not significantly increase plasma cortisol concentration in patients with primary or secondary adrenocortical insufficiency.

Target	Actions	Organism
AAdrenocorticotropic hormone receptor	antagonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Rapidly absorbed following intramuscular administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

About 15 minutes following intravenous administration.

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
Unlock Additional Data
7-Nitroindazole	The risk or severity of liver damage can be increased when Tetracosactide is combined with 7-Nitroindazole.
Acetazolamide	The risk or severity of liver damage can be increased when Tetracosactide is combined with Acetazolamide.
Amobarbital	The risk or severity of liver damage can be increased when Tetracosactide is combined with Amobarbital.
Barbexaclone	The risk or severity of liver damage can be increased when Tetracosactide is combined with Barbexaclone.
Barbital	The risk or severity of liver damage can be increased when Tetracosactide is combined with Barbital.
Beclamide	The risk or severity of liver damage can be increased when Tetracosactide is combined with Beclamide.
Brexanolone	The risk or severity of liver damage can be increased when Tetracosactide is combined with Brexanolone.
Brivaracetam	The risk or severity of liver damage can be increased when Tetracosactide is combined with Brivaracetam.
Butalbital	The risk or severity of liver damage can be increased when Tetracosactide is combined with Butalbital.
Cannabidiol	The risk or severity of liver damage can be increased when Tetracosactide is combined with Cannabidiol.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

Evidence Level

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

References

General References

Not Available

External Links

KEGG Drug: D00284
KEGG Compound: C06926
PubChem Compound: 16133751
PubChem Substance: 46506301
ChemSpider: 10481947
BindingDB: 50017180
ChEBI: 3901
ChEMBL: CHEMBL2103784
Therapeutic Targets Database: DAP000284
PharmGKB: PA164749052
Wikipedia: Tetracosactide

ATC Codes

H01AA02 — Tetracosactide

AHFS Codes

68:04.00 — Adrenals
36:04.00 — Adrenocortical Insufficiency
68:28.00 — Pituitary

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Not Yet Recruiting	Basic Science	Polycystic Ovaries Syndrome	1
0	Withdrawn	Basic Science	BMI >30 kg/m2 / Hyperandrogenemia / Polycystic Ovaries Syndrome	1
1	Completed	Basic Science	Stress	1
1	Completed	Supportive Care	Adrenal Cortex Diseases / Infant Morbidity	1
2	Recruiting	Treatment	Muscular Dystrophy, Duchenne	1
2	Recruiting	Treatment	Post-Dural Puncture Headache	1
2	Suspended	Diagnostic	Adrenal Suppression	1
3	Completed	Diagnostic	Development	1
3	Recruiting	Diagnostic	Adrenal Insufficiency / Lecithin Acyltransferase Deficiency / Liver Cirrhosis / Spur Cell Anemia	1
4	Completed	Diagnostic	Adrenal Insufficiency / Healthy Volunteers / Hypopituitarism	1
4	Completed	Treatment	Adrenal Failure	1
4	Completed	Treatment	Postdural Puncture Headache	1
4	Withdrawn	Diagnostic	Adrenal Insufficiency	1
Not Available	Active Not Recruiting	Other	Autonomic Nervous System / Baroreflexes / Stress, Physiological	1
Not Available	Active Not Recruiting	Other	Postural Tachycardia Syndrome	1
Not Available	Completed	Screening	Polycystic Ovaries Syndrome	1
Not Available	Recruiting	Basic Science	BMI >30 kg/m2 / Hyperandrogenemia / Polycystic Ovaries Syndrome	1
Not Available	Recruiting	Diagnostic	Adrenal Insufficiency	1
Not Available	Unknown Status	Screening	Brain Injury / Craniocerebral Trauma	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Amphastar Pharmaceuticals
Generamedix Inc.
Sandoz

Dosage forms

Form	Route	Strength
Injection, powder, lyophilized, for solution	Intramuscular; Intravenous; Parenteral	0.25 mg/1mL
Powder, for solution	Intramuscular; Intravenous	0.25 mg
Injection, powder, for solution	Intramuscular; Intravenous	0.25 mg/1mL
Injection, powder, lyophilized, for solution	Intramuscular; Intravenous	0.25 mg/1mL
Injection, powder, lyophilized, for solution	Intravenous	0.25 mg/1mL
Injection, solution	Intravenous	0.25 mg/1mL
Suspension	Intramuscular	1 mg

Prices

Unit description	Cost	Unit
Cortrosyn 0.25 mg vial	127.9USD	vial
Cosyntropin 0.25 mg/ml	119.91USD	ml
Cosyntropin 0.25 mg vial	115.1USD	vial
Synacthen Depot 1 mg/vial	34.77USD	vial

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0481 mg/mL	ALOGPS
logP	-0.95	ALOGPS
logP	-14	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.03	ChemAxon
pKa (Strongest Basic)	12.38	ChemAxon
Physiological Charge	6	ChemAxon
Hydrogen Acceptor Count	46	ChemAxon
Hydrogen Donor Count	42	ChemAxon
Polar Surface Area	1158.72 Å²	ChemAxon
Rotatable Bond Count	93	ChemAxon
Refractivity	790.98 m³·mol^-1	ChemAxon
Polarizability	309.35 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST): Not Available
Spectra: Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
Kingdom: Organic compounds
Super Class: Organic Polymers
Class: Polypeptides
Sub Class: Not Available
Direct Parent: Polypeptides
Alternative Parents: Peptides / Tyrosine and derivatives / Arginine and derivatives / Phenylalanine and derivatives / Histidine and derivatives / Glutamic acid and derivatives / Methionine and derivatives / Valine and derivatives / Proline and derivatives / N-acyl-L-alpha-amino acids
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Substituents: Polypeptide / Alpha peptide / Tyrosine or derivatives / Arginine or derivatives / Phenylalanine or derivatives / Histidine or derivatives / Glutamic acid or derivatives / Methionine or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid
show 61 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: polypeptide (CHEBI:3901)

Targets

Details1. Adrenocorticotropic hormone receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Melanocortin receptor activity
Specific Function: Receptor for corticotropin (ACTH). This receptor is mediated by G proteins (G(s)) which activate adenylate cyclase (cAMP).
Gene Name: MC2R
Uniprot ID: Q01718
Uniprot Name: Adrenocorticotropic hormone receptor
Molecular Weight: 33926.28 Da

References

Schwerin M, Kanitz E, Tuchscherer M, Brussow KP, Nurnberg G, Otten W: Stress-related gene expression in brain and adrenal gland of porcine fetuses and neonates. Theriogenology. 2005 Mar 1;63(4):1220-34. [PubMed:15710205]
Mehrabani PA, Bassett JR: Adrenocorticotropin binding sites in rat cardiac tissue. Pharmacol Biochem Behav. 1990 Jan;35(1):99-103. [PubMed:2156274]
Moraes RB, Czepielewski MA, Friedman G: Cortisol variation after low-dose Cortrosyn test. Crit Care Med. 2010 Jul;38(7):1612-3. doi: 10.1097/CCM.0b013e3181da4ef1. [PubMed:20562554]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on May 23, 2007 21:46 / Updated on May 24, 2019 23:02

Tetracosactide

Identification

Structure for Tetracosactide (DB01284)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References