Alprostadil


Entry
D00180                      Drug                                   
Name
Alprostadil (JP18/USP/INN);
Prostin VR pediatric (TN);
Caverject (TN);
Edex (TN);
Muse (TN)
Product
EDEX (Endo Pharmaceuticals), MUSE (Meda Pharmaceuticals), CAVERJECT IMPULSE (Pharmacia and Upjohn Company LLC), CAVERJECT (Pharmacia and Upjohn Company LLC), PROSTIN (Pharmacia and Upjohn Company LLC), CAVERJECT IMPULSE (U.S. Pharmaceuticals)
  Generic
ALPROSTADIL (Teva Parenteral Medicines)
Formula
C20H34O5
Exact mass
354.2406
Mol weight
354.481
Structure
Simcomp
Class
Hormonal agent
 DG01961  Prostaglandin derivative
  DG01611  Prostaglandin E1 derivative
Remark
Same as: C04741
Therapeutic category: 2190
ATC code: C01EA01 G04BE01
Chemical structure group: DG00239
Product (DG00239): D00180<JP/US> D02705<JP>
Efficacy
Vasodilator, Prostaglandin E1 receptor agonist
  Disease
Pulmonary atresia [DS:H01802 H01803]
Tricuspid atresia [DS:H01785]
Tetralogy of Fallot [DS:H00549]
Comment
Prostaglandin derivative
Treatment of erectile dysfunction
Target
PTGER1 [HSA:5731] [KO:K04258]
  Pathway
hsa04020  Calcium signaling pathway
hsa04080  Neuroactive ligand-receptor interaction
Interaction
Structure map
map07035  Prostaglandins
map07228  Eicosanoid receptor agonists/antagonists
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 C CARDIOVASCULAR SYSTEM
  C01 CARDIAC THERAPY
   C01E OTHER CARDIAC PREPARATIONS
    C01EA Prostaglandins
     C01EA01 Alprostadil
      D00180  Alprostadil (JP18/USP/INN) <JP/US>
 G GENITO URINARY SYSTEM AND SEX HORMONES
  G04 UROLOGICALS
   G04B UROLOGICALS
    G04BE Drugs used in erectile dysfunction
     G04BE01 Alprostadil
      D00180  Alprostadil (JP18/USP/INN) <JP/US>
USP drug classification [BR:br08302]
 Hormonal Agents, Stimulant/Replacement/Modifying (Prostaglandins)
  Alprostadil
   D00180  Alprostadil (JP18/USP/INN)
 Sexual Disorder Agents
  Sexual Disorder Agents (Male)
   Alprostadil
    D00180  Alprostadil (JP18/USP/INN)
Therapeutic category of drugs in Japan [BR:br08301]
 2  Agents affecting individual organs
  21  Cardiovascular agents
   219  Miscellaneous
    2190  Miscellaneous
     D00180  Alprostadil (JP18/USP/INN)
Drug groups [BR:br08330]
 Hormonal agent
  DG01961  Prostaglandin derivative
   DG01611  Prostaglandin E1 derivative
    DG00239  Alprostadil
     D00180  Alprostadil
Target-based classification of drugs [BR:br08310]
 G Protein-coupled receptors
  Rhodopsin family
   Prostaglandin
    PTGER1
     D00180  Alprostadil (JP18/USP/INN) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00180  Alprostadil
  D00180  Alprostadil injection
Drug groups [BR:br08330]
 Hormonal agent
  DG01961  Prostaglandin derivative
   DG01611  Prostaglandin E1 derivative
    DG00239  Alprostadil
Other DBs
CAS: 745-65-3
PubChem: 7847248
ChEBI: 15544
PDB-CCD: XPG[PDBj]
LigandBox: D00180
NIKKAJI: J3.319G
KCF data

ATOM        25
            1   C1y C    23.5830  -17.4951
            2   C1y C    23.5770  -18.9049
            3   C5x C    22.2430  -17.0640
            4   C1b C    24.7947  -16.7901
            5   C1y C    22.2604  -19.3360
            6   C2b C    24.7947  -19.5983
            7   C1x C    21.4215  -18.2057
            8   O5x O    21.8061  -15.7356
            9   C1b C    26.0066  -17.4951
            10  O1a O    21.8409  -20.6703
            11  C2b C    26.0066  -18.9049
            12  C1b C    27.2243  -16.7901
            13  C1c C    27.2243  -19.5983
            14  C1b C    28.4301  -17.4951
            15  C1b C    28.4360  -18.9049
            16  O1a O    27.2243  -21.0023
            17  C1b C    29.6477  -16.7901
            18  C1b C    29.6477  -19.5983
            19  C1b C    30.8654  -17.4951
            20  C1b C    30.8654  -18.9049
            21  C6a C    32.0773  -16.7901
            22  C1b C    32.0773  -19.5983
            23  O6a O    33.2890  -17.5009
            24  O6a O    32.0306  -15.4268
            25  C1a C    33.2950  -18.9049
BOND        25
            1     1   2 1
            2     1   3 1
            3     1   4 1 #Down
            4     2   5 1
            5     2   6 1 #Up
            6     3   7 1
            7     3   8 2
            8     4   9 1
            9     5  10 1 #Down
            10    6  11 2
            11    9  12 1
            12   11  13 1
            13   12  14 1
            14   13  15 1
            15   13  16 1 #Down
            16   14  17 1
            17   15  18 1
            18   17  19 1
            19   18  20 1
            20   19  21 1
            21   20  22 1
            22   21  23 1
            23   21  24 2
            24   22  25 1
            25    5   7 1