Pseudoephedrine

ID: ALA1590

Cas Number: 90-82-4

PubChem CID: 7028

Product Number: S472669, Order Now?

Max Phase: Approved

First Approval: 1963

Molecular Formula: C10H15NO

Molecular Weight: 165.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Acunaso | Isoephedrine, d- | Neodurasina | Pseudoephedrine | PSEUDOEPHEDRINE|(+)-Pseudoephedrine|d-Pseudoephedrine|Isoephedrine|trans-Ephedrine|d-Isoephedrine|Psi-ephedrin|Psi-ephedrine|(+)-threo-Ephedrine|d-psi-Ephedrine|Sudafed|90-82-4|L(+)-psi-Ephedrine|L-(+)-Pseudoephedrine|(+)-psi-Ephedrine|Pseudoefedrina|Pseudoephedrinum|(+)-(1S,2S)-Pseudoephedrine|(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol|Besan|(1S,2S)-(+)-Pseudoephedrine|Pseudoephedrine d-form|Neodurasina|Acunaso|Pseudoephedrine (D)|(1Show More⌵

Synonyms from Alternative Forms(32): Pseudoephedrine hydrochloride | Efidac 24 | Galsud | Otrinol | Pseudoephedrine hcl | Rhinalair | NSC-106567 | NSC-33634 | Actifed | Contac | Dimotane plus | Dimotane plus l.a. | Galpseud | Galpseud plus | Novafed | Otrivine mu-cron | Pseudophed | Sinutab | Sudafed | Sudafed 12 hour | Sudafed 12 hr decongest | Sudafed 24 hour | Sudafed plus | Sudafed-sa | Pseudoephedrine polistirex | Pseudo-12 | Pseudoephedrine sulfate | D-pseudoephedrine sulfate | Pseudoephedrine sulphate | SCH 4855 | SCH-4855 | Afrinol

Canonical SMILES:  CN[C@@H](C)[C@@H](O)c1ccccc1

Standard InChI:  InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1

Standard InChI Key:  KWGRBVOPPLSCSI-WCBMZHEXSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  1  0  0  0  0  0999 V2000
    4.5667   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -7.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -7.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -7.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -6.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -7.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -8.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -7.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -8.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -7.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -8.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  1  5  1  1
  6  2  1  0
  7  2  2  0
  8  4  1  0
  3  9  1  6
 10  6  2  0
 11  7  1  0
 12 10  1  0
 12 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1590

   PSEUDOEPHEDRINE

2. Alternative Forms:

   

   ALA1590

   PSEUDOEPHEDRINE HYDROCHLORIDE
3. 

   ALA1590

   PSEUDOEPHEDRINE POLISTIREX
4. 

   ALA1590

   PSEUDOEPHEDRINE SULFATE

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 165.24

Molecular Weight (Monoisotopic): 165.1154

AlogP: 1.33

#Rotatable Bonds: 3

Polar Surface Area: 32.26

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 9.52

CX LogP: 1.32

CX LogD: -0.78

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.71

Np Likeness Score: 0.43

References

1. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

2. Bard B, Carrupt PA, Martel S..  (2009)  Lipophilicity of basic drugs measured by hydrophilic interaction chromatography.,  52  (10): [PMID:19397318] [10.1021/jm9003945]

3. Sui X, Sun J, Li H, Wang Y, Liu J, Liu X, Zhang W, Chen L, He Z..  (2009)  Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data.,  44  (11): [PMID:19586686] [10.1016/j.ejmech.2009.06.004]

4. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

5. Gozalbes R, Pineda-Lucena A..  (2010)  QSAR-based solubility model for drug-like compounds.,  18  (19): [PMID:20810286] [10.1016/j.bmc.2010.08.003]

6. PubChem BioAssay data set, 

7. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

8. Noorizadeh H, Noorizadeh M, Farmany A.  (2012)  Advanced QSRR models of toxicological screening of basic drugs in whole blood by UPLC-TOFMS,  21  (12): [10.1007/s00044-012-9977-1]

9. Russo CM, Adhikari AA, Wallach DR, Fernandes S, Balch AN, Kerr WG, Chisholm JD..  (2015)  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5'-phosphatase (SHIP).,  25  (22): [PMID:26453006] [10.1016/j.bmcl.2015.09.034]

10. WHO Anatomical Therapeutic Chemical Classification, 

11. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

12. Unpublished dataset, 

13. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

14. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data