U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H73N21O10S2
Molecular Weight 1048.251
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETELCALCETIDE

SMILES

C[C@@H](NC(=O)[C@@H](CCCNC(N)=N)NC(=O)[C@@H](CCCNC(N)=N)NC(=O)[C@@H](CCCNC(N)=N)NC(=O)[C@@H](C)NC(=O)[C@@H](CSSC[C@H](N)C(O)=O)NC(C)=O)C(=O)N[C@H](CCCNC(N)=N)C(N)=O

InChI

InChIKey=ANIAZGVDEUQPRI-ZJQCGQFWSA-N
InChI=1S/C38H73N21O10S2/c1-18(28(62)56-22(27(40)61)8-4-12-49-35(41)42)53-30(64)23(9-5-13-50-36(43)44)58-32(66)25(11-7-15-52-38(47)48)59-31(65)24(10-6-14-51-37(45)46)57-29(63)19(2)54-33(67)26(55-20(3)60)17-71-70-16-21(39)34(68)69/h18-19,21-26H,4-17,39H2,1-3H3,(H2,40,61)(H,53,64)(H,54,67)(H,55,60)(H,56,62)(H,57,63)(H,58,66)(H,59,65)(H,68,69)(H4,41,42,49)(H4,43,44,50)(H4,45,46,51)(H4,47,48,52)/t18-,19-,21+,22-,23-,24-,25-,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula C38H73N21O10S2
Molecular Weight 1048.251
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Etelcalcetide (formerly velcalcetide, trade name Parsabiv) is a calcimimetic drug for the treatment of secondary hyperparathyroidism in patients undergoing hemodialysis. Etelcalcetide was approved (trade name Parsabiv) for the treatment of secondary hyperparathyroidism (HPT) in adult patients with chronic kidney disease (CKD) on hemodialysis in February, 2017. Etelcalcetide is a synthetic peptide calcium-sensing receptor agonist. It allosterically modulates the calcium-sensing receptor (CaSR). Etelcalcetide binds to the CaSR and enhances activation of the receptor by extracellular calcium. Activation of the CaSR on parathyroid chief cells decreases PTH secretion.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
25.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Parsabiv

Approved Use

PARSABIV is a calcium-sensing receptor agonist indicated for: Secondary hyperparathyroidism (HPT) in adult patients with chronic kidney disease (CKD) on hemodialysis.

Launch Date

2017
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
67 ng/mL
0.035 mg/kg single, intravenous
dose: 0.035 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ETELCALCETIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: UNKNOWN
food status: UNKNOWN
31.4 ng/mL
0.035 mg/kg single, intravenous
dose: 0.035 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ETELCALCETIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2700 ng × h/mL
0.035 mg/kg single, intravenous
dose: 0.035 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ETELCALCETIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: UNKNOWN
food status: UNKNOWN
955 ng × h/mL
0.035 mg/kg single, intravenous
dose: 0.035 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ETELCALCETIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.67 day
0.035 mg/kg single, intravenous
dose: 0.035 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ETELCALCETIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: UNKNOWN
food status: UNKNOWN
5.85 h
0.035 mg/kg single, intravenous
dose: 0.035 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ETELCALCETIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
unknown, unknown
ETELCALCETIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
45 mg multiple, intravenous (total weekly dose)
Studied dose
Dose: 45 mg
Route: intravenous
Route: multiple
Dose: 45 mg
Sources:
unhealthy, 61 ± 14 years
Health Status: unhealthy
Age Group: 61 ± 14 years
Sex: M+F
Sources:
5 mg 3 times / week steady, intravenous
Recommended
Dose: 5 mg, 3 times / week
Route: intravenous
Route: steady
Dose: 5 mg, 3 times / week
Sources: Page: p. 30
unhealthy
n = 503
Health Status: unhealthy
Population Size: 503
Sources: Page: p. 30
Disc. AE: Calcium decreased, Nausea...
AEs leading to
discontinuation/dose reduction:
Calcium decreased (5 patients)
Nausea (1 patient)
Vomiting (1 patient)
Chest discomfort (1 patient)
GI malformation (1 patient)
Hemiparesis (1 patient)
Hyperhidrosis (1 patient)
Sources: Page: p. 30
AEs

AEs

AESignificanceDosePopulation
Chest discomfort 1 patient
Disc. AE
5 mg 3 times / week steady, intravenous
Recommended
Dose: 5 mg, 3 times / week
Route: intravenous
Route: steady
Dose: 5 mg, 3 times / week
Sources: Page: p. 30
unhealthy
n = 503
Health Status: unhealthy
Population Size: 503
Sources: Page: p. 30
GI malformation 1 patient
Disc. AE
5 mg 3 times / week steady, intravenous
Recommended
Dose: 5 mg, 3 times / week
Route: intravenous
Route: steady
Dose: 5 mg, 3 times / week
Sources: Page: p. 30
unhealthy
n = 503
Health Status: unhealthy
Population Size: 503
Sources: Page: p. 30
Hemiparesis 1 patient
Disc. AE
5 mg 3 times / week steady, intravenous
Recommended
Dose: 5 mg, 3 times / week
Route: intravenous
Route: steady
Dose: 5 mg, 3 times / week
Sources: Page: p. 30
unhealthy
n = 503
Health Status: unhealthy
Population Size: 503
Sources: Page: p. 30
Hyperhidrosis 1 patient
Disc. AE
5 mg 3 times / week steady, intravenous
Recommended
Dose: 5 mg, 3 times / week
Route: intravenous
Route: steady
Dose: 5 mg, 3 times / week
Sources: Page: p. 30
unhealthy
n = 503
Health Status: unhealthy
Population Size: 503
Sources: Page: p. 30
Nausea 1 patient
Disc. AE
5 mg 3 times / week steady, intravenous
Recommended
Dose: 5 mg, 3 times / week
Route: intravenous
Route: steady
Dose: 5 mg, 3 times / week
Sources: Page: p. 30
unhealthy
n = 503
Health Status: unhealthy
Population Size: 503
Sources: Page: p. 30
Vomiting 1 patient
Disc. AE
5 mg 3 times / week steady, intravenous
Recommended
Dose: 5 mg, 3 times / week
Route: intravenous
Route: steady
Dose: 5 mg, 3 times / week
Sources: Page: p. 30
unhealthy
n = 503
Health Status: unhealthy
Population Size: 503
Sources: Page: p. 30
Calcium decreased 5 patients
Disc. AE
5 mg 3 times / week steady, intravenous
Recommended
Dose: 5 mg, 3 times / week
Route: intravenous
Route: steady
Dose: 5 mg, 3 times / week
Sources: Page: p. 30
unhealthy
n = 503
Health Status: unhealthy
Population Size: 503
Sources: Page: p. 30
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
A Single- and Multiple-Dose, Multicenter Study of Etelcalcetide in Japanese Hemodialysis Patients With Secondary Hyperparathyroidism.
2017 Jul
Formulary Drug Review: Etelcalcetide.
2017 Nov
Etelcalcetide: injectable calcimimetic for the treatment of secondary hyperparathyroidism in hemodialysis-dependent patients.
2017 Sep
A Decision-Analytic Model to Assess the Cost-Effectiveness of Etelcalcetide vs. Cinacalcet.
2018 May
Patents

Sample Use Guides

 Ensure corrected serum calcium is at or above the lower limit of normal prior to PARSABIV (Etelcalcetide) initiation, a PARSABIV dose increase, or re-initiation of PARSABIV therapy after a dosing interruption.  The recommended starting dose of PARSABIV is 5 mg administered by intravenous (IV) bolus injection three times per week at the end of hemodialysis treatment.  The maintenance dose of PARSABIV is individualized and determined by titration based on parathyroid hormone (PTH) and corrected serum calcium response. The maintenance dose is the dose that maintains PTH levels within the recommended target range and corrected serum calcium within the normal range. The lowest maintenance dose of PARSABIV is 2.5 mg three times per week and the highest maintenance dose of PARSABIV is 15 mg three times per week.  Administer PARSABIV only at the end of hemodialysis treatment.  If a regularly scheduled hemodialysis treatment is missed, DO NOT administer any missed doses. Resume PARSABIV at the end of the next hemodialysis treatment at the prescribed dose. If doses of PARSABIV are missed for more than 2 weeks, re-initiate PARSABIV at the recommended starting dose of 5 mg (or 2.5 mg if that was the patient’s last dose).
Route of Administration: Intravenous
Treatment of HEK-293T cells expressing the hCaSR with increasing concentrations of Etelcalcetide (AMG 416) resulted in a dose-dependent increase in IP1 accumulation with an apparent EC50 of 25 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:19:18 GMT 2023
Edited
by admin
on Fri Dec 15 20:19:18 GMT 2023
Record UNII
60ME133FJB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETELCALCETIDE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
ETELCALCETIDE [MI]
Common Name English
TELCALCETIDE
Common Name English
Etelcalcetide [WHO-DD]
Common Name English
ONO-5163
Code English
VELCALCETIDE
Common Name English
N-ACETYL-D-CYSTEINYL-D-ALANYL-D-ARGINYL-D-ARGINYL-D-ARGINYL-D-ALANYL-D-ARGININAMIDE DISULFIDE WITH L-CYSTEINE
Common Name English
etelcalcetide [INN]
Common Name English
KAI-4169
Code English
PARSABIV
Brand Name English
ETELCALCETIDE [USAN]
Common Name English
D-ARGININAMIDE, N-ACETYL-D-CYSTEINYL-D-ALANYL-D-ARGINYL-D-ARGINYL-D-ARGINYL-D-ALANYL-, DISULFIDE WITH L-CYSTEINE
Common Name English
AMG-416
Code English
ETELCALCETIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-ATC H05BX04
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
NCI_THESAURUS C78275
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
FDA ORPHAN DRUG 567616
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
NDF-RT N0000175902
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
Code System Code Type Description
FDA UNII
60ME133FJB
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
PUBCHEM
71511839
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
DRUG BANK
DB12865
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
WIKIPEDIA
Etelcalcetide
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
EVMPD
SUB178987
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL3545184
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID70155132
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
SMS_ID
100000164426
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
DAILYMED
60ME133FJB
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
USAN
ZZ-124
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
NCI_THESAURUS
C129712
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
DRUG CENTRAL
5181
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
MERCK INDEX
m11978
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
CAS
1262780-97-1
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
INN
9809
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
RXCUI
1876119
Created by admin on Fri Dec 15 20:19:18 GMT 2023 , Edited by admin on Fri Dec 15 20:19:18 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
Etelcalcetide is primarily bound to plasma albumin and the plasma non-covalent protein binding is less than 50%.
BINDING
TARGET -> AGONIST
Related Record Type Details
METABOLITE LESS ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC